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Quantum chemical conformational analysis of the auxin phytohormone 4‐methyl‐3‐indole acetic acid
Author(s) -
Ramek Michael,
Tomić Sanja
Publication year - 1999
Publication title -
international journal of quantum chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.484
H-Index - 105
eISSN - 1097-461X
pISSN - 0020-7608
DOI - 10.1002/(sici)1097-461x(1999)75:6<1003::aid-qua4>3.0.co;2-v
Subject(s) - mindo , mndo , chemistry , auxin , quantum chemical , computational chemistry , potential energy surface , acetic acid , indole test , stereochemistry , indole 3 acetic acid , maxima and minima , molecule , organic chemistry , biochemistry , mathematical analysis , mathematics , gene
The potential energy surface of 4‐methyl‐3‐indole acetic acid (IAA) was investigated via RHF/6‐31G* calculations. Five symmetry‐unique local minima with syn‐periplanar orientation of the COOH group are present. In contrast, unsubstituted IAA and 4‐Cl‐IAA have only four such minima. The shape of the energy surface is different in all three cases, and that of 4‐Me‐IAA is found to contain elements of both reference compounds. Semiempirical energy surfaces (AM1, PM3, MNDO, and MINDO/3), which were determined too, differ significantly among each other and from the restricted Hartree–Fock (RHF) one. ©1999 John Wiley & Sons, Inc. Int J Quant Chem 75: 1003–1008, 1999