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From Single Molecule to Crystal: Mapping Out the Conformations of Tartaric Acids and Their Derivatives
Author(s) -
Janiak Agnieszka,
Rychlewska Urszula,
Kwit Marcin,
Stępień Urszula,
Gawrońska Krystyna,
Gawroński Jacek
Publication year - 2012
Publication title -
chemphyschem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.016
H-Index - 140
eISSN - 1439-7641
pISSN - 1439-4235
DOI - 10.1002/cphc.201200033
Subject(s) - molecule , tartaric acid , chemistry , single crystal , crystallography , stereochemistry , computational chemistry , organic chemistry , citric acid
Stereoisomers of one of the most important organic compounds, tartaric acid, optically active and meso as well as the ester or amide derivatives, can show diverse structures related to the rotation around the three carbon–carbon bonds. This study determines the controlling factors for conformational changes of these molecules in vacuo, in solution, and in the crystalline state using DFT calculations, spectroscopic measurements, and X‐ray diffraction. All structural variations can be logically accounted for by the possibility of formation and breaking of hydrogen bonds between the hydroxy or amide donors and oxygen acceptors, among these the hydrogen bonds that close five‐membered rings being the most stable. These findings are useful in designing molecular and crystal structures of highly polar, polyfunctional, chiral compounds.