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Comparative ab initio SCF conformational study of 4‐chloro‐indole‐3‐acetic acid and indole‐3‐acetic acid phytohormones (auxins)
Author(s) -
Ramek Michael,
Tomić Sanja,
KojićProdić Biserka
Publication year - 1996
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(1996)60:8<1727::aid-qua1>3.0.co;2-#
Subject(s) - auxin , indole test , indole 3 acetic acid , chemistry , ab initio , acetic acid , computational chemistry , stereochemistry , organic chemistry , biochemistry , gene
An ab initio conformational analysis of 4‐chloroindole‐3‐acetic acid was performed at the RHF/6‐311G * * level. The mirror symmetrical conformer (in which the indole ring is coplanar with the COOH group) is most stable; next in energy are the two conformers with the C—COOH fragment perpendicular to the indole ring with relative energies of 2.72 and 6.69 kJ/mol. H(SINGLEBOND)Cl hydrogen bonding results in only a minor stabilization. The results are combined with those obtained earlier for indole‐3‐acetic acid and recent biological data regarding auxin (growth hormone) activity. From this, assumptions concerning the biologically active conformation are drawn. © 1996 John Wiley & Sons, Inc.