The DOI matches its Crossref record; 33 of the 33 references it cites were found in a registry or an index.
Effects of Heteroatoms on Aromatic π−π Interactions: Benzene−Pyridine and Pyridine Dimer
Abstract
Heteroatoms are found in many noncovalent complexes which are of biological importance. The effect of heteroatoms on pi-pi interactions is assessed via highly accurate quantum chemical computations for the two simplest cases of interactions between aromatic molecules containing heteroatoms, namely, benzene-pyridine and pyridine dimer. Benchmark quality estimated coupled-cluster through perturbative triples [CCSD(T)] binding energies are computed near the complete basis set limit. Comparisons to the benzene dimer are made to determine the contributions from heteroatoms. The presence of a heteroatom reduces the spatial extent of the pi-electron cloud and polarizability of pyridine as compared to benzene. As a result, the magnitude of the dispersion, exchange, and induction interactions in benzene-pyridine and pyridine dimer is generally reduced as compared to those for the benzene dimer. Benzene-pyridine and pyridine dimer bind more strongly than the benzene dimer in several configurations, and in contrast to the benzene dimer, parallel-displaced configurations can be significantly preferred over T-shaped configurations. Hydrogens para to a heteroatom are more effective "pi-hydrogen bond" donors, but aromatic rings with heteroatoms are worse "pi-hydrogen bond" acceptors.
Overview
The claims and statistics of this paper haven’t been checked yet.
Run the check — free, no account needed. It reads the open-access text and checks the sources it cites.
Integrity signals
Registry
Cites
Statistics
Verification
Claims the paper makes
The claims and statistics of this paper haven’t been checked yet.
Run the check — free, no account needed. It reads the open-access text and checks the sources it cites.
Self-check
Percentages, sums and reported differences re-computed from the paper’s own numbers.
The self-check needs the paper’s full text.
Citations
Cites
Dunning, T. H. (1989) · The Journal of Chemical Physics · doi:10.1063/1.456153 · Cited by 31,648
Boys, S. F., & Bernardi, F. (1970) · Molecular Physics · doi:10.1080/00268977000101561 · Cited by 22,188
Electron affinities of the first-row atoms revisited. Systematic basis sets and wave functions
Kendall, R. A., Dunning, T. H., & Harrison, R. J. (1992) · The Journal of Chemical Physics · doi:10.1063/1.462569 · Cited by 15,496
A fifth-order perturbation comparison of electron correlation theories
Raghavachari, K., Trucks, G. W., Pople, J. A., & Head-Gordon, M. (1989) · Chemical Physics Letters · doi:10.1016/s0009-2614(89)87395-6 · Cited by 8,504
Principles of Nucleic Acid Structure
Saenger, W. (1984) · Springer Advanced Texts in Chemistry · doi:10.1007/978-1-4612-5190-3 · Cited by 4,150
Interactions with Aromatic Rings in Chemical and Biological Recognition
Meyer, E. A., Castellano, R. K., & Diederich, F. (2003) · Angewandte Chemie International Edition · doi:10.1002/anie.200390319 · Cited by 3,541
Perturbation Theory Approach to Intermolecular Potential Energy Surfaces of van der Waals Complexes
Jeziorski, B., Moszynski, R., & Szalewicz, K. (1994) · Chemical Reviews · doi:10.1021/cr00031a008 · Cited by 2,818
Aromatic-Aromatic Interaction: A Mechanism of Protein Structure Stabilization
Burley, S. K., & Petsko, G. A. (1985) · Science · doi:10.1126/science.3892686 · Cited by 2,524
Grimme, S. (2003) · The Journal of Chemical Physics · doi:10.1063/1.1569242 · Cited by 1,746
Estimates of the Ab Initio Limit for π−π Interactions: The Benzene Dimer
Sinnokrot, M. O., Valeev, E. F., & Sherrill, C. D. (2002) · Journal of the American Chemical Society · doi:10.1021/ja025896h · Cited by 1,339
Self-citation
Cited by
Mardirossian, N., & Head-Gordon, M. (2017) · Molecular Physics · doi:10.1080/00268976.2017.1333644 · Cited by 2,307
Aromatic Rings in Chemical and Biological Recognition: Energetics and Structures
Salonen, L. M., Ellermann, M., & Diederich, F. (2011) · Angewandte Chemie International Edition · doi:10.1002/anie.201007560 · Cited by 1,539
Mardirossian, N., & Head-Gordon, M. (2014) · Physical Chemistry Chemical Physics · doi:10.1039/c3cp54374a · Cited by 986
Riley, K. E., Pitoňák, M., Jurečka, P., & Hobza, P. (2010) · Chemical Reviews · doi:10.1021/cr1000173 · Cited by 759
Sui, S.-F. (2021) · Annual Review of Biophysics · doi:10.1146/annurev-biophys-062920-063657 · Cited by 72
Metadata
- Authors
- Hohenstein, E. G., & Sherrill, C. D.
- Venue
- The Journal of Physical Chemistry A
- Publisher
- American Chemical Society (ACS)
- Published
- 2009-01-08
- Volume
- 113
- Issue
- 5
- Pages
- 878-886
- ISSN
- 1089-5639 (ISSN-L)
- 1520-5215
- OpenAlex
- W2084773273
- Cited by
- 373
- References
- 33
- FWCI
- 17.33
- Type
- journal article
- Language
- en
- Open access
- closed
About these checks
Registry, retraction, Cites and statistics results are computed, not judged, with one exception: a printed reference that no index lists is read once by a model before it counts as a citation error. Claims are extracted by a model and kept only when their quote appears verbatim in the text; each cited source is then checked, with a model’s help, for whether it says what the claim relies on. Those verdicts can be wrong — read the claim’s quote and the cited source before relying on one.
Statistics and arithmetic are recomputed, not judged.
Confidence bands are shown only for fields calibrated on our annotated test set. None is calibrated yet, so no band is shown.
What counts as a claim ›How we measure confidence ›How we check this ›
Are you an author, or do you see a problem with this page? Request a review
Data sources
Bibliographic data: Semantic Scholar, OpenAlex, Crossref.
Contains information from the Semantic Scholar Academic Graph Datasets, made available under the ODC Attribution License (ODC-BY 1.0).
Semantic Scholar’s data is described in: Kinney, R., et al. (2023). The Semantic Scholar Open Data Platform. arXiv:2301.10140.
