Evaluating Competing Intermolecular Interactions through Molecular Electrostatic Potentials and Hydrogen-Bond Propensities
Bhupinder Sandhu
1
,
Ann Mclean
1
,
Abhijeet Sinha
1
,
John Desper
1
,
Amy A. Sarjeant
2
,
Shyam Vyas
2
,
2
The Cambridge Crystallographic Data Centre, Piscataway, New Jersey 08854, United States
|
3
Small Molecule Design & Development, Eli Lilly and Company, Indianapolis, Indiana 46285, United States
|
Publication type: Journal Article
Publication date: 2017-12-05
scimago Q2
wos Q1
SJR: 0.633
CiteScore: 5.6
Impact factor: 3.4
ISSN: 15287483, 15287505
General Chemistry
Condensed Matter Physics
General Materials Science
Abstract
The structural chemistry of six thiazole amides has been explored using experimental crystallographic data, and a combination of calculated hydrogen-bond propensities (HBPs) and hydrogen-bond energies. Both methods correctly identify the main hydrogen-bonded synthon, a pairwise N–H···N dimer, which appears in all the available structures. The strength and stability of the homosynthon in these compounds were tested by attempting to co-crystallize all six compounds with 20 different carboxylic acids. A total of 120 attempted reactions were carried out via liquid-assisted grinding experiments; sixty of these reactions produced a co-crystal, as indicated by IR spectroscopy. HBP calculations were employed in order to try to predict which of the 120 reactions would be successful. A multi-component score (MC score) was obtained from the hydrogen-bond propensity calculations, and this score coupled with a cut-off value >0.0 resulted in a 77% agreement between prediction and experiment (88% success for aliphatic a...
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44
Total citations:
44
Citations from 2024:
9
(20%)
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MLA
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GOST
Copy
Sandhu B. et al. Evaluating Competing Intermolecular Interactions through Molecular Electrostatic Potentials and Hydrogen-Bond Propensities // Crystal Growth and Design. 2017. Vol. 18. No. 1. pp. 466-478.
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Sandhu B., Mclean A., Sinha A., Desper J., Sarjeant A. A., Vyas S., Reutzel-Edens S. M., Aakeröy C. Evaluating Competing Intermolecular Interactions through Molecular Electrostatic Potentials and Hydrogen-Bond Propensities // Crystal Growth and Design. 2017. Vol. 18. No. 1. pp. 466-478.
Cite this
RIS
Copy
TY - JOUR
DO - 10.1021/acs.cgd.7b01458
UR - https://doi.org/10.1021/acs.cgd.7b01458
TI - Evaluating Competing Intermolecular Interactions through Molecular Electrostatic Potentials and Hydrogen-Bond Propensities
T2 - Crystal Growth and Design
AU - Sandhu, Bhupinder
AU - Mclean, Ann
AU - Sinha, Abhijeet
AU - Desper, John
AU - Sarjeant, Amy A.
AU - Vyas, Shyam
AU - Reutzel-Edens, Susan M.
AU - Aakeröy, Christer
PY - 2017
DA - 2017/12/05
PB - American Chemical Society (ACS)
SP - 466-478
IS - 1
VL - 18
SN - 1528-7483
SN - 1528-7505
ER -
Cite this
BibTex (up to 50 authors)
Copy
@article{2017_Sandhu,
author = {Bhupinder Sandhu and Ann Mclean and Abhijeet Sinha and John Desper and Amy A. Sarjeant and Shyam Vyas and Susan M. Reutzel-Edens and Christer Aakeröy},
title = {Evaluating Competing Intermolecular Interactions through Molecular Electrostatic Potentials and Hydrogen-Bond Propensities},
journal = {Crystal Growth and Design},
year = {2017},
volume = {18},
publisher = {American Chemical Society (ACS)},
month = {dec},
url = {https://doi.org/10.1021/acs.cgd.7b01458},
number = {1},
pages = {466--478},
doi = {10.1021/acs.cgd.7b01458}
}
Cite this
MLA
Copy
Sandhu, Bhupinder, et al. “Evaluating Competing Intermolecular Interactions through Molecular Electrostatic Potentials and Hydrogen-Bond Propensities.” Crystal Growth and Design, vol. 18, no. 1, Dec. 2017, pp. 466-478. https://doi.org/10.1021/acs.cgd.7b01458.
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