CoChat
Sign Up
Cited by 52

The DOI matches its Crossref record.

Azine-Hydrazone Tautomerism of Guanylhydrazones: Evidence for the Preference Toward the Azine Tautomer

Chourasiya, Sumit S., Kathuria, Deepika, Nikam, Sampada S., Ramakrishnan, Ashok, Khullar, Sadhika, Mandal, Sanjay K., Chakraborti, Asit K., Bharatam, Prasad V.·2016·The Journal of Organic Chemistry
DOI 10.1021/acs.joc.6b01258
Open this paper in CoChat — free account

Abstract

Guanylhydrazones have been known for a long time and have wide applications in organic synthesis, medicinal chemistry, and material science; however, little attention has been paid toward their electronic and structural properties. Quantum chemical analysis on several therapeutically important guanylhydrazones indicated that all of them prefer the azine tautomeric state (by about 3-12 kcal/mol). A set of simple and conjugated azines were designed using quantum chemical methods, whose tautomeric preference toward the azine tautomer is in the range of 3-8 kcal/mol. Twenty new azines were synthesized and isolated in their neutral state. Variable temperature NMR study suggests existence of the azine tautomer even at higher temperatures with no traces of the hydrazone tautomer. The crystal structures of two representative compounds confirmed that the title compounds prefer to exist in their azine tautomeric form.

Overview

Integrity signals

Registry

Crossref · 10.1021/acs.joc.6b01258

Cites

Statistics

Recomputing p-values needs the paper’s full text.

Verification

Claims the paper makes

This paper’s full text isn’t openly available, so its claims and self-check weren’t run. The registry and citation checks still apply.

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?

Citations

Cites

No references could be resolved yet.

Research works printed but not linked: 78

  1. 10.1021/cr60081a003 · DOI
  2. 10.1021/jm00163a049 · DOI
  3. 10.1021/jm00301a006 · DOI
  4. 10.1021/jm50017a013 · DOI
  5. 10.1021/jm00291a022 · DOI
  6. 10.1021/jm00367a007 · DOI
  7. 10.1021/jm00396a020 · DOI
  8. 10.1016/0223-5234(91)90107-X · DOI
  9. 10.1016/S0960-894X(99)00632-0 · DOI
  10. 10.1016/0223-5234(94)90064-7 · DOI
  11. 10.1021/jm00292a004 · DOI
  12. 10.1021/jm0109309 · DOI
  13. 10.1016/0006-2952(70)90323-0 · DOI
  14. 10.1002/jps.2600790615 · DOI
  15. 10.1021/jm00266a025 · DOI
  16. 10.1021/jm00201a010 · DOI
  17. 10.1016/j.ejmech.2003.09.012 · DOI
  18. 10.1016/j.ejmech.2011.07.001 · DOI
  19. 10.1021/jm061077m · DOI
  20. 10.1021/jm00053a007 · DOI
  21. 10.1016/0301-4622(90)80016-Z · DOI
  22. 10.1124/mol.107.035832 · DOI
  23. 10.1124/jpet.109.154997 · DOI
  24. 10.1016/j.jsb.2011.09.008 · DOI
  25. 10.1517/17460441.2013.788496 · DOI
  26. 10.1016/j.febslet.2011.08.050 · DOI
  27. 10.3987/COM-98-8162 · DOI
  28. 10.1002/anie.196304591 · DOI
  29. 10.1039/C4NJ01175A · DOI
  30. 10.1039/C5RA05574A · DOI
  31. 10.1515/znb-1993-1219 · DOI
  32. 10.1016/0006-2952(85)90179-0 · DOI · Paper page
  33. 10.1007/BF00808279 · DOI
  34. 10.1007/PL00010271 · DOI
  35. 10.1107/S160053680603399X · DOI
  36. 10.1016/j.bmc.2010.10.008 · DOI
  37. 10.1039/c19670001137 · DOI
  38. 10.1021/jo00977a049 · DOI
  39. 10.1021/jo402497v · DOI
  40. 10.1021/ol402796m · DOI
  41. 10.1021/ol501483k · DOI
  42. 10.1002/anie.200250571 · DOI
  43. 10.1021/ja01165a031 · DOI
  44. 10.1021/jo011117o · DOI
  45. 10.1039/b706964b · DOI
  46. 10.1039/P29950002311 · DOI
  47. 10.1039/B404129A · DOI
  48. 10.1080/02678290802028773 · DOI
  49. 10.1021/jp972607g · DOI
  50. 10.1063/1.353837 · DOI
  51. 10.1021/jp407623u · DOI
  52. 10.1021/ci3001277 · DOI
  53. 10.1021/jm0104567 · DOI
  54. 10.1016/j.ultsonch.2012.02.009 · DOI
  55. 10.1155/2012/802408 · DOI
  56. 10.1016/j.molcata.2005.08.039 · DOI
  57. 10.1016/j.molcata.2006.07.018 · DOI
  58. 10.1016/j.ultsonch.2009.06.013 · DOI
  59. 10.3390/molecules19055806 · DOI
  60. 10.1016/j.ejmech.2014.09.055 · DOI
  61. 10.1016/j.bmc.2013.01.051 · DOI
  62. 10.1016/0223-5234(89)90077-9 · DOI
  63. 10.1080/00387018908053866 · DOI
  64. 10.1021/ol102422h · DOI
  65. 10.1021/ol4016089 · DOI
  66. 10.1021/ol060479l · DOI
  67. 10.1021/acs.orglett.5b03317 · DOI
  68. 10.1021/jo902358c · DOI
  69. 10.1021/jo200411f · DOI
  70. 10.1021/ja00732a022 · DOI
  71. 10.1016/S0166-1280(98)00191-2 · DOI
  72. 10.1002/jcc.21323 · DOI
  73. Frisch M. J., 2009, Gaussian 09
  74. Parr R. G., 1989, Density-Functional Theory of Atoms and Molecules
  75. 10.1103/PhysRevB.37.785 · DOI · Paper page
  76. 10.1063/1.474659 · DOI
  77. 10.1021/ja970990x · DOI
  78. 10.1002/mrc.1299 · DOI

Cited by

Sorted by citations

See all 52

Metadata

Authors
Chourasiya, S. S., Kathuria, D., Nikam, S. S., Ramakrishnan, A., Khullar, S., Mandal, S. K., Chakraborti, A. K., & Bharatam, P. V.
Venue
The Journal of Organic Chemistry
Publisher
American Chemical Society (ACS)
Published
2016-08-24
Volume
81
Issue
17
Pages
7574-7583
ISSN
  • 0022-3263
  • 1520-6904
DOI
10.1021/acs.joc.6b01258
Cited by
52
References
0
Language
en
Funders
Department of Science and Technology, Ministry of Science and Technology

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