Double Aromaticity in Monocyclic Carbon, Boron, and Borocarbon Rings Based on Magnetic Criteria
Open accessAbstract
Demonstrates double-aromatic character in monocyclic carbon, boron, and borocarbon rings using NICS analyses. Two mutually orthogonal Hückel p AO frameworks: familiar pi orbitals augmented by in-plane delocalization of radial p orbitals. Double aromaticity present in C6, C10, C14.
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- Findingnone given
Planar C7 monocycle has mixed aromatic (p) and antiaromatic (radial) systems.
“Planar C 7 and C 9 monocycles have mixed aromatic (p) and antiaromatic (radial) systems.”
Quote in the paperSubstantial claim - Findingnone given
Planar C9 monocycle has mixed aromatic (p) and antiaromatic (radial) systems.
“Planar C 7 and C 9 monocycles have mixed aromatic (p) and antiaromatic (radial) systems.”
Quote in the paperSubstantial claim - Findingown data
The isotropic NICS(0) value of D6h C6 (−36.9) is larger than the −24.0 NICS(0)iso of the D3h minimum.
“Surprisingly, the isotropic NICS(0) value of the less stable D 6h C 6 (À36.9) is appreci-ably larger than the À24.0 NIC-S(0) iso of the D 3h minimum (Table 1).”
Quote in the paperSubstantial claim - Findingown data
A NICS_zz grid dissected into p and radial contributions for D3h-C6 shows a change from paratropic within the central triangle to diatropic within the outer triangles.
“However, a grid of NICS zz points, dissected into p and radial contributions, shows a clear change from paratropic within the central triangle to diatropic within the outer triangles and, as expected for aromatic systems, a deshielding zone outside the molecular framework (Figure 6, an isotropic grid is given in Figure 2 in the Supporting Information).”
Quote in the paperSubstantial claim - Findingown data
The overall aromatic character of C6H3+, C6^4+, and C4B4^4+ is dominated by diatropic 6p electron systems that are similar in all three ions (NICS_pzz ~ −34).
“However, the overall aromatic character is dominated by the diatropic 6p electron systems, which are similar in all three ions (NICS pzz % À34).”
Quote in the paperSubstantial claim
- Findingnone given
At the B3LYP/6-311+G(d) level, the interconversion barrier between the D3h and D6h structures of C6 is 13.6 kcal mol−1.
“At the B3LYP/6-311+G(d) level, the interconversion barrier between the D 3h and D 6h structures is 13.6 kcal mol À1 .”
Quote in the paperNot a substantial claim - Findingown data
The double-aromatic character of selected monocyclic carbon, boron, and borocarbon rings is demonstrated by refined NICS analyses involving the contributions of individual canonical MOs and their out-of-plane NICS tensor component (CMO-NICS_zz).
“The double-aromatic character of selected monocyclic carbon, boron, and borocarbon rings is demonstrated by refined nucleus-independent chemical shift (NICS) analyses involving the contributions of individual canonical MOs and their out-of-plane NICS tensor component (CMO-NICS zz ).”
Quote in the paperSubstantial claim - Findingown data
C6^4+ and C4B4^4+ have a more diatropic in-plane radial orbital (NICS_radzz ~ −15) than C6H3+ (NICS_radzz = −5.3).
“All three possess a single diatropic in-plane radial orbital, which is more diatropic in the tetracations (NICS radzz % À15) than in C 6 H 3 + (NICS radzz = À5.3).”
Quote in the paperSubstantial claim - Findingown data
Monocyclic C12 is doubly antiaromatic, as both the orthogonal p and radial Hückel sets are paratropic.
“Monocyclic C 8 and C 12 are doubly antiaromatic, as both the orthogonal p and radial Hückel sets are paratropic.”
Quote in the paperSubstantial claim - Findingown data
Monocyclic C8 is doubly antiaromatic, as both the orthogonal p and radial Hückel sets are paratropic.
“Monocyclic C 8 and C 12 are doubly antiaromatic, as both the orthogonal p and radial Hückel sets are paratropic.”
Quote in the paperSubstantial claim - Findingcitation
C8 has a smaller ionization potential than C6 or C10.
“Not surprisingly, C 8 has a smaller ionization potential than C 6 or C 10 .[149]”
Quote in the paperNot a substantial claim0 of 1 sources checked- cites [149] 149. S. B. H. Bach, J. R. Eyler, J. Chem. Phys. 1990, 92, 358 -363. source
- Findingown data
For larger borocarbons, NICS pzz values decrease in magnitude as more boron atoms are inserted into the ring (C8B4 -37.2, C7B5 -29.3, and C6B8 -28.6).
“but these values decrease in magnitude as more boron atoms are inserted into the ring (C 8 B 4 À37.2, C 7 B 5 À29.3, and C 6 B 8 À28.6).”
Quote in the paperNot a substantial claim- Rests on an assumption: The NICS zz tensor components and their dissection into p and radial contributions reliably diagnose double aromaticity and antiaromaticity.
- Findingnone given
For borocarbons, the larger rings have smaller NICS pzz values (C6B8 < C7B6 < C8B4 < C9B2).
“For borocarbons the larger rings have smaller NICS pzz values (C 6 B 8 < C 7 B 6 < C 8 B 4 < C 9 B 2 ).”
Quote in the paperSubstantial claim- Rests on an assumption: The NICS zz tensor components and their dissection into p and radial contributions reliably diagnose double aromaticity and antiaromaticity.
- Findingown data
NICS analyses establishes double aromaticity in the two boron and eight borocarbon rings studied here.
“The previously described NICS analyses also establishes double aromaticity in the two boron and eight borocarbon rings studied here (see Figure 13 and Table 1).”
Quote in the paperSubstantial claim - Findingown data
The out-of-plane NICS zz tensor components provide clear evidence for double antiaromaticity in C8 and C12, each containing two orthogonal eight electron systems.
“but also for double antiaromaticity (C 8 and C 12 , each containing two orthogonal eight electron systems)”
Quote in the paperSubstantial claim- Rests on an assumption: The NICS zz tensor components and their dissection into p and radial contributions reliably diagnose double aromaticity and antiaromaticity.
- Findingown data
The out-of-plane NICS zz tensor components (NICS pzz and NICS radzz) provide clear evidence for double aromaticity in C6, C6^4+, C10, and C14.
“their out-of-plane NICS zz tensor components (NICS pzz and NICS radzz ) provide clear evidence not only for double aromaticity (C 6 , C 6 4 + , C 10 , and C 14 )”
Quote in the paperSubstantial claim- Rests on an assumption: The NICS zz tensor components and their dissection into p and radial contributions reliably diagnose double aromaticity and antiaromaticity.
- Findingown data
C9B2 has the most diatropic p system among the larger borocarbons (NICS pzz = -40.3).
“C 9 B 2 has the most diatropic p system”
Quote in the paperNot a substantial claim- Rests on an assumption: The NICS zz tensor components and their dissection into p and radial contributions reliably diagnose double aromaticity and antiaromaticity.
- Findingreasoning
The NICS zz values of B10^2- and B12 for both the perpendicular p and the in-plane radial systems are similar to those of 6+6 borocarbons.
“their NICS zz values for both the perpendicular p and the in-plane radial systems are similar to those of 6+6 borocarbons.”
Quote in the paperSubstantial claim- Rests on an assumption: The NICS zz tensor components and their dissection into p and radial contributions reliably diagnose double aromaticity and antiaromaticity.
- Findingown data
The highest lying p MO (HOMO) and highest in-plane radial orbital (HOMO−1) dominate the overall molecular paratropicity of C8.
“As expected, the highest lying p MO (the HOMO), and the highest in-plane radial orbital (HOMOÀ1), dominate the overall molecular paratropicity (Figure 10).”
Quote in the paperSubstantial claim - Findingnone given
Unlike the C10 carbon monocycle, the frontier orbital symmetry of B10^2- does not result in a second-order Jahn-Teller distortion.
“Unlike the C 10 carbon monocycle, the frontier orbital symmetry of B 10 2À does not result in a secondorder Jahn-Teller distortion”
Quote in the paperNot a substantial claim - Findingnone given
Increasing ring size and the number of Hückel electrons of carbon clusters results in larger NICS zz values for each system (for example, C14 > C10 > C6).
“Increasing ring size and the number of Hückel electrons of carbon clusters results in larger NICS zz values for each system (for example, C 14 > C 10 > C 6 ).”
Quote in the paperNot a substantial claim- Rests on an assumption: The NICS zz tensor components and their dissection into p and radial contributions reliably diagnose double aromaticity and antiaromaticity.
- Findingown data
The NICS radzz values of systems with two in-plane radial electrons overlap with those containing six in-plane radial electrons.
“The NICS radzz values of systems with two in-plane radial electrons overlap with those containing six in-plane radial electrons.”
Quote in the paperSubstantial claim- Rests on an assumption: The NICS zz tensor components and their dissection into p and radial contributions reliably diagnose double aromaticity and antiaromaticity.
- Findingreasoning
The highest possible D10h ring symmetry is favored for B10^2-.
“the highest possible D 10h ring symmetry is favored.”
Quote in the paperSubstantial claim - Findingown data
The in-plane radial system (NICS radzz) values for C9B2, C7B6, and C6B8 range from -21.1 to -28.4.
“In contrast, the in-plane radial system (NICS radzz ) values for C 9 B 2 , C 7 B 6 , and C 6 B 8 range from À21.1 to À28.4.”
Quote in the paperSubstantial claim- Rests on an assumption: The NICS zz tensor components and their dissection into p and radial contributions reliably diagnose double aromaticity and antiaromaticity.
- Findingown data
The highly symmetric D4h C8B4 possesses an exceptionally diatropic in-plane radial system (NICS radzz -42.9).
“The highly symmetric D 4h C 8 B 4 possesses an exceptionally diatropic in-plane radial system (NICS radzz À42.9).”
Quote in the paperSubstantial claim- Rests on an assumption: The NICS zz tensor components and their dissection into p and radial contributions reliably diagnose double aromaticity and antiaromaticity.
- Findingnone given
The NICS pzz values decrease with an increasing electron number and increasing ring size (for example, the p system of C12 is less paratropic than that of C8).
“In contrast, the NICS pzz values decrease with an increasing electron number and increasing ring size (for example, the p system of C 12 is less paratropic than that of C 8 ; Scheme 1).”
Quote in the paperNot a substantial claim- Rests on an assumption: The NICS zz tensor components and their dissection into p and radial contributions reliably diagnose double aromaticity and antiaromaticity.
- Findingown data
C4B4 illustrates a 6+6 doubly aromatic borocarbon system.
“C 4 B 4 illustrates a 6+6 doubly aromatic borocarbon system (Figure 14).”
Quote in the paperSubstantial claim - Findingown data
The 10 radial electron C8B4 shows remarkable in-plane diatropic character, nearly equal to that of the 14 in-plane electron C14.
“The 10 radial electron C 8 B 4 shows remarkable in-plane diatropic character, nearly equal to that of the 14 in-plane electron C 14 .”
Quote in the paperSubstantial claim- Rests on an assumption: The NICS zz tensor components and their dissection into p and radial contributions reliably diagnose double aromaticity and antiaromaticity.
- Findingown data
For C5B2, the in-plane radial system is paratropic at the center but becomes strongly diatropic at distances as close as 0.5 away.
“the in-plane radial system is paratropic at the center but becomes strongly diatropic at distances as close as 0.5 away (Supporting Information, Figure 2).”
Quote in the paperSubstantial claim- Rests on an assumption: The NICS zz tensor components and their dissection into p and radial contributions reliably diagnose double aromaticity and antiaromaticity.
- Findingreasoning
B10^2- and B12 monocyclic boron rings are doubly aromatic, as expected from their 6+6 electron count.
“As expected from their 6+6 electron count, the B 10 2À and B 12 monocyclic boron rings are doubly aromatic”
- Also stated in: § Conclusion · plain
“B 10 2À and B 12 monocyclic rings also exhibit double aromaticity, but are not the most stable isomers.[26]”
Quote in the paperSubstantial claim- Rests on an assumption: The NICS zz tensor components and their dissection into p and radial contributions reliably diagnose double aromaticity and antiaromaticity.
- Also stated in: § Conclusion · plain
- Findingown data
The out-of-plane NICS zz tensor components provide clear evidence for mixed aromaticity/antiaromaticity in C7 and C9.
“and for mixed aromaticity/antiaromaticity (C 7 and C 9 ; Table 1).”
Quote in the paperSubstantial claim- Rests on an assumption: The NICS zz tensor components and their dissection into p and radial contributions reliably diagnose double aromaticity and antiaromaticity.
- Findingown data
For C5B2, the perpendicular p system remains diatropic at all positions within the ring.
“The perpendicular p system remains diatropic at all positions within the ring.”
Quote in the paperSubstantial claim- Rests on an assumption: The NICS zz tensor components and their dissection into p and radial contributions reliably diagnose double aromaticity and antiaromaticity.
- Findingnone given
For antiaromatic systems, smaller ring systems possessing fewer radial electrons have smaller NICS radzz values than larger ring systems with more radial electrons.
“For antiaromatic systems, smaller ring systems possessing fewer radial electrons have smaller NICS radzz values than larger ring systems with more radial electrons.”
Quote in the paperNot a substantial claim- Rests on an assumption: The NICS zz tensor components and their dissection into p and radial contributions reliably diagnose double aromaticity and antiaromaticity.
- Findingown data
C5B2, like D3h C6, is doubly aromatic according to the NICS zz grid.
“The NICS zz grid shows that C 5 B 2 , like D 3h C 6 , is doubly aromatic.”
Quote in the paperSubstantial claim- Rests on an assumption: The NICS zz tensor components and their dissection into p and radial contributions reliably diagnose double aromaticity and antiaromaticity.
- Findingreasoning
C9 has mixed p aromatic/in-plane antiaromatic character with a 10+8 system.
“Similarly, C 9 has mixed p aromatic/in-plane antiaromatic character with a 10+8 system.”
Quote in the paperSubstantial claim - Findingnone given
Overlap of NICS pzz values is seen in systems containing six and 10 p electrons.
“Overlap of NICS pzz values is also seen in systems containing six and 10 p electrons.”
Quote in the paperNot a substantial claim- Rests on an assumption: The NICS zz tensor components and their dissection into p and radial contributions reliably diagnose double aromaticity and antiaromaticity.
- Findingnone given
The NICS radzz values correlate weakly with the number of radial electrons.
“The NICS radzz values correlate weakly with the number of radial electrons.”
Quote in the paperNot a substantial claim- Rests on an assumption: The NICS zz tensor components and their dissection into p and radial contributions reliably diagnose double aromaticity and antiaromaticity.
- Findingown data
The NICS radzz grids for the D6h form of C6 are diatropic overall.
“In contrast, the NICS radzz grids for the D 6h form are diatropic overall.”
Quote in the paperSubstantial claim- Rests on an assumption: The NICS zz tensor components and their dissection into p and radial contributions reliably diagnose double aromaticity and antiaromaticity.
- Findingown data
The NICS pzz grids indicate the p systems to be diatropic inside rings.
“The NICS pzz grids indicate the p systems to be diatropic inside rings.”
Quote in the paperSubstantial claim- Rests on an assumption: The NICS zz tensor components and their dissection into p and radial contributions reliably diagnose double aromaticity and antiaromaticity.
- Findingown data
C4B4^4+ is doubly aromatic like C6^4+.
“Indeed, CMO-NICS zz shows C 4 B 4 4 + to be doubly aromatic like C 6 4 + .”
Quote in the paperSubstantial claim - Findingown data
In C4B4, the NICS(0)_zz of all three in-plane (radial) orbitals are diatropic.
“In contrast to C 6 , another 6+6 system (Figure 8) with somewhat smaller isotropic NICS(0) and NICS(1) values, the NICS(0) zz of all three in-plane (radial) orbitals of C 4 B 4 are diatropic.”
Quote in the paperSubstantial claim - Findingreasoning
NICS iso, NICS zz, and CMO-NICS zz values show that the overall diatropic character of doubly aromatic compounds is greater than that of their singly aromatic counterparts.
“NICS iso , NICS zz , and CMO-NICS zz values show the overall diatropic character of doubly aromatic compounds is greater than their singly aromatic counterparts.”
Quote in the paperSubstantial claim- Rests on an assumption: The NICS zz tensor components and their dissection into p and radial contributions reliably diagnose double aromaticity and antiaromaticity.
- Premisecitation
Cyclic C6 prefers D3h symmetry over both the D6h and the linear chain forms.
“The most recent theoretical investigations conclude that cyclic C 6 prefers D 3h symmetry over both the D 6h and the linear chain forms (Figure 4).[68,77]”
Quote in the paperNot a substantial claim0 of 2 sources checked- cites [68] 68. J. Hutter, H. P. Lüthi, J. Chem. Phys. 1994, 101, 2213.
Couldn’t be matched to a paper in Crossref, so it can’t be checked.
- cites [77] 77. V. Pless, H. U. Suter, B. Engels, J. Chem. Phys. 1994, 101, 4042 - 4048.
Couldn’t be matched to a paper in Crossref, so it can’t be checked.
- Interpretationreasoning
The large difference between isotropic NICS(0) and NICS(1) values of C6H3+ indicates the system contains a diatropic Hückel system in the molecular plane.
“The large difference between isotropic NICS(0) and NICS(1) values indicates that the system contains a diatropic Hückel system in the molecular plane.”
Quote in the paperSubstantial claim - Interpretationown data
The NICS_zz grid reveals the doubly aromatic nature of D3h C6.
“The NICS zz grid reveals the doubly aromatic nature of D 3h C 6 .”
Quote in the paperSubstantial claim - Interpretationown data
NICS(0)iso values do not predict the relative stability of D6h and D3h C6.
“The NICS(0) iso values do not predict the relative stability of the two forms.”
Quote in the paperSubstantial claim - Interpretationown data
Double aromaticity in these rings results from two mutually orthogonal Hückel p AO frameworks in a single molecule, with familiar p orbitals augmented by in-plane delocalization of electrons occupying radial p orbitals.
“The double aromaticity considered results from two mutually or-thogonal Hückel p AO frameworks in a single molecule.The familiar p orbitals are augmented by the in-plane delocalization of electrons occupying sets of radial (rad) p orbitals.”
Quote in the paperSubstantial claim - Interpretationown data
C6H3+ is doubly aromatic.
“The C 6 H 3 + ion: The distorted [79] C 6 H 3 + ion (Figures 1 and 4), the doubly aromatic prototype, was predicted by Chandrasekhar, Jemmis, and Schleyer in 1979 [1] and computed at higher levels in 1994.[38]”
Quote in the paperSubstantial claim0 of 2 sources checked- cites [1] 1. J. Chandrasekhar, E. D. Jemmis, P. v. R. Schleyer, Tetrahedron Lett. 1979, 20, 3707.
Couldn’t be matched to a paper in Crossref, so it can’t be checked.
- cites [38] 38. P. v. R. Schleyer, H. J. Jiao, M. N. Glukhovtsev, J. Chandrasekhar, E. Kraka, J. Am. Chem. Soc. 1994, 116, 10 129.
Couldn’t be matched to a paper in Crossref, so it can’t be checked.
- Premisecitation
The polycyclic B10/B12 isomers also exhibit double aromaticity.
“These polycyclic isomers also exhibit double aromaticity.”
Quote in the paperNot a substantial claim0 of 1 sources checked- cites [26] 26. A. N. Alexandrova, A. I. Boldyrev, H.-J. Zhai, L.-S. Wang, Coord. Chem. Rev. 2006, 250, 2811.
Couldn’t be matched to a paper in Crossref, so it can’t be checked.
- Rests on an assumption: The NICS zz tensor components and their dissection into p and radial contributions reliably diagnose double aromaticity and antiaromaticity.
- Premisecitation
MP2 results were found to be qualitatively incorrect.
“MP2 results were found to be qualitatively incorrect.[76]”
Quote in the paperSubstantial claim0 of 1 sources checked- cites [76] 76. J. M. L. Martin, J. El-Yazal, J.-P. FranÅois, Chem. Phys. Lett. 1996, 252, 9.
Couldn’t be matched to a paper in Crossref, so it can’t be checked.
- Study design and conductreasoning
There is a strong basis set dependence for the use of CMO-NICS; large Pople-type basis sets result in large divergence from results obtained using IGLO-III, Karlsruhe, and smaller Pople basis sets.
“We have observed a strong basis set dependence for the use of CMO-NICS.”
- Also stated in: § References · plain
“Large Pople-type basis sets (for example, 6-311+G- A C H T U N G T R E N N U N G (2d,2p) and 6-311+GA C H T U N G T R E N N U N G (3df,2p)) result in large divergence from re- sults obtained by using IGLO-III, Karlsruhe, and smaller Pople basis sets.”
Quote in the paperNot a substantial claim - Also stated in: § References · plain
- Interpretationreasoning
The second additional set of in-plane delocalized electrons increases the total diatropicity.
“The second additional set of inplane delocalized electrons increases the total diatropicity.”
Quote in the paperSubstantial claim - Premisecitation
Small monocyclic rings containing odd numbers of carbon atoms (Cn, n = 5-9) are higher in energy than the corresponding linear structures.
“Martin et al. [76] showed by using DFT and CCSD(T) calculations that small monocyclic rings containing odd numbers of carbon atoms (C n , n = 5-9) are higher in energy than the corresponding linear structures.”
Quote in the paperNot a substantial claim0 of 1 sources checked- cites [76] 76. J. M. L. Martin, J. El-Yazal, J.-P. FranÅois, Chem. Phys. Lett. 1996, 252, 9.
Couldn’t be matched to a paper in Crossref, so it can’t be checked.
- Premisecitation
Cyclic C7 and C9 prefer C2v over planar structures at both the CCSD(T) and B3LYP levels.
“Cyclic C 7 and C 9 prefer C 2v over planar structures at both the CCSD(T) and B3LYP levels.[150]”
Quote in the paperNot a substantial claim0 of 1 sources checked- cites [150] 150. The structures of C 7 and C 9 tested for aromaticity are not minima on the potential energy surface. Received: January 29, 2007 Published online: April 12, 2007
Couldn’t be matched to a paper in Crossref, so it can’t be checked.
- Interpretationreasoning
In general, dissection of NICS(0) values suffices to identify double aromaticity.
“C 6 and C 5 B 2 are atypical cases requiring NICS grids to identify their double aromaticity; in general, dissection of NICS(0) values suffice for this purpose.”
Quote in the paperSubstantial claim- Rests on an assumption: The NICS zz tensor components and their dissection into p and radial contributions reliably diagnose double aromaticity and antiaromaticity.
- Premisecitation
DFT geometries and relative energies are in reasonable agreement with results using high-order correlation methods.
“Nevertheless, DFT geometries and relative energies are in reasonable agreements with results using high-order correlation methods (for example, coupled-cluster expansion).[68,74,76]”
Quote in the paperSubstantial claim0 of 3 sources checked- cites [68] 68. J. Hutter, H. P. Lüthi, J. Chem. Phys. 1994, 101, 2213.
Couldn’t be matched to a paper in Crossref, so it can’t be checked.
- cites [74] 74. J. M. L. Martin, P. R. Taylor, J. Phys. Chem. 1996, 100, 6047 -6056.
Couldn’t be matched to a paper in Crossref, so it can’t be checked.
- cites [76] 76. J. M. L. Martin, J. El-Yazal, J.-P. FranÅois, Chem. Phys. Lett. 1996, 252, 9.
Couldn’t be matched to a paper in Crossref, so it can’t be checked.
- Interpretationown data
C6 and C5B2 are atypical cases that require NICS grids to identify their double aromaticity.
“C 6 and C 5 B 2 are atypical cases requiring NICS grids to identify their double aromaticity; in general, dissection of NICS(0) values suffice for this purpose.”
Quote in the paperSubstantial claim- Rests on an assumption: The NICS zz tensor components and their dissection into p and radial contributions reliably diagnose double aromaticity and antiaromaticity.
- Interpretationreasoning
The basis set dependence of CMO-NICS results from a poor balance of the larger Pople basis sets (low ratio of sp/d functions).
“This results from a poor balance of the larger Pople basis sets (low ratio of sp/d functions).”
Quote in the paperNot a substantial claim - Interpretationown data
The enhanced diatropicity of the radial system compensates for the reduction in diatropic character of the C4B4 p system compared to both isomers of C6.
“The enhanced diatropicity of the radial system compensates for the reduction in diatropic character of the C 4 B 4 p system (see the CMO-NICS pzz data) as compared to both isomers of C 6 (Figure 8).”
Quote in the paperSubstantial claim - Premisecitation
The C4h cyclic form of C8 lies only 4 kcal mol−1 below the linear structure at CCSD(T)/cc-pVDZ.
“CCSD(T)/cc-pVDZ calculations predict the C 4h cyclic form to lie only 4 kcal mol À1 below the linear structure.[74]”
Quote in the paperNot a substantial claim0 of 1 sources checked- cites [74] 74. J. M. L. Martin, P. R. Taylor, J. Phys. Chem. 1996, 100, 6047 -6056.
Couldn’t be matched to a paper in Crossref, so it can’t be checked.
- Interpretationreasoning
The double aromaticity of the C4B4^4+, C4B4, C5B2, C2B8, C9B2, C8B4, C7B6, and C6B8 borocarbon rings should result in considerable stability, at least as local minima.
“The doubly aromaticity of the C 4 B 4 4 + , C 4 B 4 , C 5 B 2 , C 2 B 8 , C 9 B 2 , C 8 B 4 , C 7 B 6 , and C 6 B 8 borocarbon rings should result in considerable stability, at least as local minima”
Quote in the paperSubstantial claim- Rests on an assumption: Double aromaticity confers considerable stability on a ring.
- Premisecitation
Polycyclic B10 (as well as B12) structural alternatives are more stable than the monocyclic forms.
“However, polycyclic B 10 (as well as B 12 ) structural alternatives are more stable than the monocyclic forms.[26]”
- Also stated in: § Conclusion · plain
“B 10 2À and B 12 monocyclic rings also exhibit double aromaticity, but are not the most stable isomers.[26]”
Quote in the paperSubstantial claim0 of 1 sources checked- cites [26] 26. A. N. Alexandrova, A. I. Boldyrev, H.-J. Zhai, L.-S. Wang, Coord. Chem. Rev. 2006, 250, 2811.
Couldn’t be matched to a paper in Crossref, so it can’t be checked.
- Also stated in: § Conclusion · plain
- May combine two claims. 21
- Classified as probably not a substantial claim. 3
May combine two claims.
Findingown dataDouble aromaticity is present in B3−, C6H3+, C6^4+, C4B4^4+, C6, C5B2, C4B4, C2B8, B10^2−, B12, C10, C9B2, C8B4, C7B6, C6B8, and C14.
“Such double aromaticity is present in B 3 À , C 6 H 3 + , C 6 4 + , C 4 B 4 4 + , C 6 , C 5 B 2 , C 4 B 4 , C 2 B 8 , B 10 2À , B 12 , C 10 , C 9 B 2 , C 8 B 4 , C 7 B 6 , C 6 B 8 , and C 14 .”
Quote in the paperSubstantial claimMay combine two claims.
Findingown dataCMO-NICS and CMO-NICS_zz show C6H3+ has a strongly aromatic six-electron p system (NICS_p = −32.8) and a weakly diatropic two-electron in-plane radial system (NICS_rad = −3.6).
“The individual canonical molecular orbital contributions to NICS (CMO-NICS) as well as each out-ofplane NICS tensor component (CMO-NICS zz ), summarized in Table 1 and Figure 5, do indeed show the presence of a strongly aromatic six-electron p system perpendicular to the molecular plane, NICS p = À32.8 and a weakly diatropic twoelectron in-plane radial system, NICS rad = À3.6 (Figure 5).”
Quote in the paperSubstantial claimMay combine two claims.
Findingown dataC6^4+ and C4B4^4+ are 6+2 doubly aromatic systems akin to C6H3+.
“As a result, the three species have relatively similar NICS zz (> À56) values and are doubly aromatic.”
Quote in the paperSubstantial claimMay combine two claims.
FindingcitationNICS_pzz of C10 and C14 are similar to their parent annulenes, but their enhanced total NICS_zz indicates an additional diatropic subsystem.
“NICS pzz of both C 10 and C 14 are similar to those of their parent annulenes [145] (for example, C 10 H 10 and C 14 H 14 ), but their enhanced total NICS zz indicates the presence of an additional diatropic subsystem.”
Quote in the paperSubstantial claim0 of 1 sources checked- cites [145] 145. We have calculated NICS on D 10h and D 14h C 10 H 10 and C 14 H 14 due to their structural similarities with monocyclic C 10 and C 14 .
Couldn’t be matched to a paper in Crossref, so it can’t be checked.
May combine two claims.
FindingreasoningC10 and C14 are doubly aromatic.
“CMO-NICS and CMO-NICS zz analysis indeed confirms that both carbon monocyclics are doubly aromatic.[15,16]”
Quote in the paperSubstantial claim0 of 2 sources checked- cites [15] 15. T. Torelli, L. Mitas, Phys. Rev. Lett. 2000, 85, 1702.
Couldn’t be matched to a paper in Crossref, so it can’t be checked.
- cites [16] 16. S. M. Martin-Santamaria, H. S. Rzepa, Chem. Commun. 2000, 1503.
Couldn’t be matched to a paper in Crossref, so it can’t be checked.
May combine two claims.
FindingreasoningC6H3+, C6^4+, and C4B4^4+ have relatively similar NICS_zz (> −56) values and are doubly aromatic.
“As a result, the three species have relatively similar NICS zz (> À56) values and are doubly aromatic.”
Quote in the paperSubstantial claimMay combine two claims.
Findingown dataC6H3+ has large negative isotropic NICS(0) of −42.3 and NICS(1) of −19.1, indicating a diatropic ring current.
“A large negative isotropic NICS(0) of À42.3 and À19.1 for NICS(1) (isotropic NICS taken at 1 above the ring center, Table 1) indicates the presence of a diatropic ring current.”
Quote in the paperSubstantial claimMay combine two claims.
Findingown dataD3h-C6 is p aromatic and radial antiaromatic at the ring center.
“This suggests that D 3h -C 6 is p aromatic and radial antiaromatic.”
Quote in the paperSubstantial claimMay combine two claims.
Findingown dataC10 and C14 contain a diatropic in-plane radial system, so their total NICS_zz is much greater (>30 ppm) than that of their annulene analogues.
“However, C 10 and C 14 also contain a diatropic in-plane radial system, thus their total NICS zz is much greater (> 30 ppm) than that of their annulene analogues (Table 1).”
Quote in the paperSubstantial claimMay combine two claims.
FindingcitationC8 is a double antiaromatic polyinic ring, possessing orthogonal eight radial + eight p-electron systems.
“C 8 is an interesting example of a double antiaromatic polyinic ring, [66,67,70,74,81] possessing orthogonal eight radial + eight-p-electron systems (Figure 4).”
Quote in the paperSubstantial claim0 of 5 sources checked- cites [66] 66. K. Raghavachari, J. S. Binkley, J. Chem. Phys. 1987, 87, 2191.
Couldn’t be matched to a paper in Crossref, so it can’t be checked.
- cites [67] 67. V. I. Baranovski, Chem. Phys. Lett. 2005, 408, 429.
Couldn’t be matched to a paper in Crossref, so it can’t be checked.
- cites [70] 70. V. Parasuk, J. Almlçf, Theor. Chim. Acta 1992, 83, 227.
Couldn’t be matched to a paper in Crossref, so it can’t be checked.
- cites [74] 74. J. M. L. Martin, P. R. Taylor, J. Phys. Chem. 1996, 100, 6047 -6056.
Couldn’t be matched to a paper in Crossref, so it can’t be checked.
- cites [81] 81. J. M. L. Martin, J. El-Yazal, J.-P. FranÅois, Chem. Phys. Lett. 1995, 242, 570.
Couldn’t be matched to a paper in Crossref, so it can’t be checked.
May combine two claims.
Findingown dataThe two-electron in-plane radial system of C4B4^4+ has enhanced diatropicity (CMO-NICS_radzz: −13.45) relative to C6H3+ (−5.30) and is closer to C6^4+ (−15.99).
“The two-electron inplane radial system has enhanced diatropicity (CMO-NICS radzz : À13.45) relative to the prototype double aromatic C 6 H 3 + (À5.30) and is closer to the C 6 4 + value (À15.99).”
Quote in the paperSubstantial claimMay combine two claims.
Findingown dataThe NICS radzz grids of D3h C6 indicate the radial system to be paratropic in the central triangle and diatropic in the outer triangles.
“The NICS radzz grids of D 3h C 6 indicate the radial system to be paratropic in the central triangle and diatropic in the outer triangles.”
Quote in the paperSubstantial claim- Rests on an assumption: The NICS zz tensor components and their dissection into p and radial contributions reliably diagnose double aromaticity and antiaromaticity.
May combine two claims.
Findingnone givenThe six p and 10 p electrons range from -23.9 to -39.5 and from -28.6 to -40.3, respectively.
“The six p and 10 p electrons range from À23.9 to À39.5 and from À28.6 to À40.3, respectively.”
Quote in the paperNot a substantial claim- Rests on an assumption: The NICS zz tensor components and their dissection into p and radial contributions reliably diagnose double aromaticity and antiaromaticity.
May combine two claims.
Findingown dataC5B2 has two orthogonal six-electron systems, with both diatropic (p) and paratropic (radial) character.
“Like D 3h -C 6 , C 5 B 2 has two orthogonal six-electron systems, with both diatropic (the p system) and paratropic (in-plane radial system) character.”
Quote in the paperSubstantial claimMay combine two claims.
Findingnone givenThe 14 p and radial electron C14 has both the largest NICS pzz (-56.7) and the most diatropic in-plane radial system (NICS radzz = -44.5).
“However, the 14 p and radial electron C 14 has both the largest NICS pzz (À56.7) and the most diatropic inplane radial system (NICS radzz = À44.5).”
Quote in the paperNot a substantial claim- Rests on an assumption: The NICS zz tensor components and their dissection into p and radial contributions reliably diagnose double aromaticity and antiaromaticity.
May combine two claims.
Findingown dataThe C6h ring of C12 exhibits the same double antiaromatic character as C8; no electronic rearrangement to a double aromatic configuration (4n+2, 4m−2) is seen.
“Regardless of the relative energies, the C 6h ring structure exhibits the same double antiaromatic character as C 8 (see Figure 11 and Table 1), no electronic rearrangement to a double aromatic configuration (4n+2, 4mÀ2) is seen.”
Quote in the paperSubstantial claimMay combine two claims.
Findingown dataThe negative overall isotropic NICS values of C7 indicate a diatropic ring current, but CMO-NICS/CMO-NICS_zz reveals a mixed aromatic/antiaromatic 6p/8 in-plane system.
“The negative overall isotropic NICS values of C 7 indicate a diatropic ring current, but CMO-NICS/CMO-NICS zz reveals a mixed aromatic/antiaromatic 6p/8 in-plane system (Supporting Information, Figure 1).”
Quote in the paperSubstantial claimMay combine two claims.
Findingown dataMany monocyclic boron, carbon, and borocarbon rings examined in Table 1 have negative isotropic NICS(0) values, but the individual p and s (in-plane radial) MO contributions (CMO-NICS) reveal diverse behavior.
“While many of the monocyclic boron, carbon, and borocarbon rings examined in Table 1 have negative isotropic NICS(0) values, the individual p and s (in-plane radial) MO contributions (CMO-NICS) reveal diverse behavior.”
Quote in the paperSubstantial claim- Rests on an assumption: The NICS zz tensor components and their dissection into p and radial contributions reliably diagnose double aromaticity and antiaromaticity.
May combine two claims.
Findingown dataThe larger borocarbons with 10+10 double aromatic systems have widely varying NICS pzz values, all of which are smaller than those of D10h [10]annulene (-46.2).
“The larger borocarbons, with 10+10 double aromatic systems, show widely varying NICS pzz values, all of which are smaller than those of D 10h [10]annulene (À46.2).”
Quote in the paperNot a substantial claim- Rests on an assumption: The NICS zz tensor components and their dissection into p and radial contributions reliably diagnose double aromaticity and antiaromaticity.
Classified as probably not a substantial claim. May combine two claims.
PremisecitationNICS provides a simple and effective magnetic aromaticity index; negative (diatropic) NICS values indicate magnetic aromaticity, while positive (paratropic) values indicate magnetic antiaromaticity.
“Introduced in 1996 by Schleyer et al., [125] NICS provides a simple and effective magnetic aromaticity index; negative (diatropic) NICS values indicate magnetic aromaticity, while positive (paratropic) values indicate magnetic antiaromaticity.”
Quote in the paperSubstantial claim0 of 1 sources checked- cites [125] 125. P. v. R. Schleyer, C. Maerker, A. Dransfeld, H. J. Jiao, N. J. R. v. E. Hommes, J. Am. Chem. Soc. 1996, 118, 6317.
Couldn’t be matched to a paper in Crossref, so it can’t be checked.
Probably not a substantial claim: may not pass S3 (load-bearing), S4 (based).
Study design and conductnone givenThe structures of C7 and C9 tested for aromaticity are not minima on the potential energy surface.
“The structures of C 7 and C 9 tested for aromaticity are not minima on the potential energy surface.”
Quote in the paperNot a substantial claimClassified as probably not a substantial claim.
PremisereasoningThe monocyclic and generally higher-symmetry carbon, boron, and borocarbon rings selected for this study had two potential double aromatic 4n+2 or double antiaromatic 4n electron systems (p and in-plane radial) based on simple electron counting expectations.
“The monocyclic and generally higher-symmetry carbon, boron, and borocarbon rings selected for this study had two potential double aromatic 4n+2 or double antiaromatic 4n electron systems (p and in-plane radial) based on simple electron counting expectations.”
Quote in the paperSubstantial claim- The authors state this as an assumption: Two valence electrons of both boron and carbon are assigned to the s framework, leaving boron with one and carbon with two available electrons for p and in-plane radial bonding.
May combine two claims.
InterpretationreasoningC4B4^4+ has slightly longer bond lengths than C4B4, likely attributable to increased Coulomb repulsion and decreased in-plane bonding character.
“C 4 B 4 4 + has slightly longer bond lengths than C 4 B 4 (Figure 13), likely attributable to increased Coulomb repulsion and decreased inplane bonding character.”
Quote in the paperNot a substantial claim
The authors state this as an assumption.
Two valence electrons of both boron and carbon are assigned to the s framework, leaving boron with one and carbon with two available electrons for p and in-plane radial bonding.
“Two valence electrons of both boron and carbon are assigned to the s framework, leaving boron with one and carbon with two available electrons for p and in-plane radial bonding.”
The paper relies on this without support.
The NICS zz tensor components and their dissection into p and radial contributions reliably diagnose double aromaticity and antiaromaticity.
“their out-of-plane NICS zz tensor components (NICS pzz and NICS radzz ) provide clear evidence not only for double aromaticity”
The paper relies on this without support.
Double aromaticity confers considerable stability on a ring.
“The doubly aromaticity of the C 4 B 4 4 + , C 4 B 4 , C 5 B 2 , C 2 B 8 , C 9 B 2 , C 8 B 4 , C 7 B 6 , and C 6 B 8 borocarbon rings should result in considerable stability, at least as local minima”
Claims other papers make about this one
Each is checked against this paper’s own text: does it say what the citing paper says it does?
The double aromaticity of small carbon rings and related boron-carbon molecules was confirmed with the CMO-NICS analysis put forth by Schleyer et al.
“The double aromaticity of small carbon rings and related boron-carbon molecules was also confirmed with the CMO-NICS analysis put forth by Schleyer et al. 32”
From Induced magnetic field in sp-hybridized carbon rings: analysis of double aromaticity and antiaromaticity in cyclo[2 <i>N</i> ]carbon allotropes (2020) · cites this paper as [32]
Self-check
Percentages, sums and reported differences re-computed from the paper’s own numbers.
Each contradiction between two passages listed here was confirmed by an independent check.
Borocarbon formula differs between the discussion and table
MinorThe discussion labels the borocarbon with a NICS pzz value near −29.3 as C7B5, whereas Table 1 assigns that value to C7B6.
“C 8 B 4 À37.2, C 7 B 5 À29.3, and C 6 B 8 À28.6”
“| C 7 B 6 | | | C 2v | 10 | 10 | À22.04 | À18.50 | À56.53 | À14.75 | À9.15 | À29.33 | À26.16 | |”
C14 radial NICS value is not the most diatropic listed
MinorThe stated radial value of −44.5 corresponds to the D7h C14 structure. Table 1 also lists a more negative radial value, −63.95, for D14h C14, so −44.5 is not the most diatropic value in the table.
“the 14 p and radial electron C 14 has both the largest NICS pzz (À56.7) and the most diatropic inplane radial system (NICS radzz = À44.5).”
“| C 14 | | | D 14h | 14 | 14 | À40.84 | À34.34 | À114.11 | À22.93 | À21.28 | À56.71 | À63.95 | |”
C12 is assigned eight electrons per system instead of twelve
MinorThe conclusion says C8 and C12 each have eight electrons in both orthogonal systems. Table 1 assigns C12 twelve electrons in each system.
“double antiaromaticity (C 8 and C 12 , each containing two orthogonal eight electron systems)”
“| C 12 | | | C 6h | 12 | 12 | + 56.92 | + 47.05 | + 180.56 | + 38.52 | + 16.79 | + 131.10 | + 49.43 | |”
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Boron-nitrogen analogues of cyclo[18]carbon
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“Akin to c-C6 (D3h) the c-C10 (D5h) cluster was also proved to be a double (σ + π)-aromatic molecule with enhanced aromaticity due to an additional diatropic subsystem (the diatropic in-plane radial system) [16].”
BackgroundInfluentialTsipis, A. C. (2016) · Coordination Chemistry Reviews · doi:10.1016/j.ccr.2016.08.005 · Cited by 32 · see citing works
RetractedThe σ delocalization in planar boron clusters
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σ‐Aromaticity in a Fully Unsaturated Ring
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Peverati, R., Bera, P. P., Lee, T. J., & Head‐Gordon, M. (2016) · The Astrophysical Journal · doi:10.3847/0004-637x/830/2/128 · Cited by 24 · see citing works
“…et al. 1994) identified this isomer as the global minimum on the +C H6 3 potential energy surface, while several other studies confirmed its double aromatic character by means of orbital analysis and nuclear independent chemical shifts (NICS) calculations (Nguyen et al. 2005; Wodrich et al. 2007).”
BackgroundAromaticity/Antiaromaticity in “Bare” and “Ligand-Stabilized” Rings of Metal Atoms
Tsipis, C. A. (2010) · Structure and bonding · doi:10.1007/978-3-642-05243-9_7 · Cited by 22 · see citing works
“Bottled” spiro-doubly aromatic trinuclear [Pd 2 Ru] + complexes
Kulichenko, M., Fedik, N. S., Monfredini, A., et al. (2020) · Chemical Science · doi:10.1039/d0sc04469e · Cited by 20 · see citing works
Seal, P. (2008) · Journal of Molecular Structure THEOCHEM · doi:10.1016/j.theochem.2008.09.019 · Cited by 20 · see citing works
Searching for double σ- and π-aromaticity in borazine derivatives
Pino‐Rios, R., Vásquez‐Espinal, A., Yáñez, O., & Tiznado, W. (2020) · RSC Advances · doi:10.1039/d0ra05939k · Cited by 18 · see citing works
Aromaticity and Antiaromaticity: How to Define Them
Baranac-Stojanović, M. (2025) · Chemistry · doi:10.3390/chemistry7040127 · Cited by 14 · see citing works
Magnetically induced current density in triple-layered beryllium–boron clusters
Đorđević, S., & Radenković, S. (2019) · Physical Chemistry Chemical Physics · doi:10.1039/c9cp00541b · Cited by 14 · see citing works
Exploration of structures and stability of planar C B3 (n= 1–8)
Shao, J., Chun-yan, H., Shi, R., Wang, C., Zhu, X., & Lü, X. (2010) · Journal of Molecular Structure THEOCHEM · doi:10.1016/j.theochem.2010.08.036 · Cited by 13 · see citing works
Magnetic Aromaticity of Cycloporphyrin Nanorings
Landi, A., Summa, F. F., & Monaco, G. (2021) · Chemistry · doi:10.3390/chemistry3030071 · Cited by 13 · see citing works
“This competition is not the result of the contributions of different subsets of active orbitals, such as the “πin” and “πout” in some carbomers [65,66] or the σ and π in periodoannulenes [67], although it must be recognized that the πin orbital set can be divided into those localized on the butadiene links and on the…”
BackgroundSynthesis and structures of monocyclic 1,4-diaza-2,3-diborine species
Söyleyici, H. C., Uyanık, S., Sevinçek, R., Fırıncı, E., Bursalı, B., Burgaz, O., Aygün, M., & Şahin, Y. (2015) · Inorganic Chemistry Communications · doi:10.1016/j.inoche.2015.09.016 · Cited by 12 · see citing works
(Anti)aromaticity of Cyclo[2<i>n</i>]Carbons (<i>n</i> = 3–12)
Baranac‐Stojanović, M. (2025) · Chemistry – An Asian Journal · doi:10.1002/asia.202500295 · Cited by 11 · see citing works
Theoretical study of the solvent effect on the aromaticity of benzene: a NICS analysis
Junqueira, G. M. A., & Santos, H. F. D. (2014) · Journal of Molecular Modeling · doi:10.1007/s00894-014-2152-5 · Cited by 11 · see citing works
Exploration on the structure, stability, and isomerization of planar C n B5 (n = 1−7) clusters
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The distortivity of π-electrons in conjugated boron rings
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Structure and stability of B 5 C and C 5 B clusters
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Formation and Stability of C6H3+Isomers
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Search for structures, potential energy surfaces, and stabilities of planar BnP(n = 1 ∼ 7)
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“In addition, there exist σ-radial MO15 and σ-tangential MO14 for 3a [18, 59 ].”
Density functional theory study of B n C clusters
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Multiple Aromaticity, Multiple Antiaromaticity, and Conflicting Aromaticity in Planar Clusters
Zubarev, D. Y., & Boldyrev, A. I. (2010) · Science and technology of atomic, molecular, condensed matter & biological systems · doi:10.1016/b978-0-444-53440-8.00005-7 · Cited by 8 · see citing works
Neural network atomistic potentials for global energy minima search in carbon clusters
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Isolierung und Reaktivität eines s‐Block‐Metall‐Antiaromaten
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Does oligomerization in fused thiophene affect reactivity and aromaticity?
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Remote Stereoelectronic Effects
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Orbital contributions to the magnetic shielding of cyclo[2 <i>n</i> ]carbons ( <i>n</i> = 3–12)
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Effects of inorganic substitutions on electronic transport properties of single-molecule devices
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Investigation of1H NMR Chemical Shifts of Organic Dye with Hydrogen Bonds and Ring Currents
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“A similar increase in bond angle is found in the double aromatic [39] C6H3 cation.”
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Structures and aromaticity of X2Y 2 − (X = C, Si, Ge and Y = N, P, As) anions
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Does P and Se doping effect molecular properties of S,N-heteroacene?
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Silyliumylidene Ion Stabilized by Two σ‐Donating Ni(0)‐ and Pd(0)‐Fragments
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A careful scrutiny of the aromaticity in anionic polynitrogen clusters
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Adjusting quantum interference in single-molecule field-effect transistors by heteroatoms
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Aromaticity of singlet and triplet states of sandwich-like alkaline earth metal-doped boron clusters
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- Authors
- Wodrich, M. D., Corminboeuf, C., Park, S. S., & Schleyer, P. V. R.
- Affiliations
- University of Georgia (US)
- Venue
- Chemistry - A European Journal
- Publisher
- Wiley
- Published
- 2007-05-15
- Volume
- 13
- Issue
- 16
- Pages
- 4582-4593
- ISSN
- 0947-6539 (ISSN-L)
- 1521-3765
- OpenAlex
- W2170596123
- Cited by
- 71
- References
- 152
- Citations by year
- 2026: 1 · 2025: 8 · 2024: 3 · 2023: 3 · 2022: 2 · 2021: 1 · 2020: 7 · 2019: 3 · 2018: 2 · 2017: 1 · 2016: 6 · 2015: 3 · 2014: 4 · 2013: 1 · 2012: 1
- FWCI
- 3.79
- Type
- journal article
- Language
- en
- Open access
- bronze
- doi.org
- Locations
- Chemistry - A European Journal (publishedVersion)
- PubMed (publishedVersion)
- Infoscience (Ecole Polytechnique Fédérale de Lausanne) (submittedVersion)
- Infoscience (Ecole Polytechnique Fédérale de Lausanne) (submittedVersion, cc-by-nc-nd)
- Funders
- National Science Foundation (0209857)
- University of Georgia
- American Chemical Society Petroleum Research Fund
- Division of Chemistry
- Topics
- Physical Sciences › Chemistry › Organic Chemistry › Synthesis and Properties of Aromatic Compounds
- Health Sciences › Medicine › Radiology, Nuclear Medicine and Imaging › Boron Compounds in Chemistry
- Physical Sciences › Chemistry › Inorganic Chemistry › Synthesis and characterization of novel inorganic/organometallic compounds
- Keywords
- double aromaticity, canonical molecular orbitals, antiaromaticity, aromaticity, boron clusters, carbon clusters
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