Electronic structure and conformation of glyphosate: an ab initio MO study

An extensive theoretical investigation on the conformations of commercially important herbicide compound, Glyphosate, have been made at the ab initio HF/3-21G* level of theory. The fully optimized structure and rotational potential around the active site nitrogen (about the C–N and N–C bond) were ex...

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Bibliographic Details
Published in:Journal of molecular structure. Theochem 2002-11, Vol.618 (1), p.117-125
Main Authors: Kaliannan, P, Mohamed Naseer Ali, M, Seethalakshmi, T, Venuvanalingam, P
Format: Article
Language:English
Subjects:
Geometry optimization
Glyphosate
Potential energy surface
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Summary:An extensive theoretical investigation on the conformations of commercially important herbicide compound, Glyphosate, have been made at the ab initio HF/3-21G* level of theory. The fully optimized structure and rotational potential around the active site nitrogen (about the C–N and N–C bond) were examined in detail. The ab initio data indicate that the most stable conformation of glyphosate is the gg − arrangement of the central dihedral angles ( Φ and Ψ). Also, most of the predicted bioactive conformers fall on the gg conformation. The present study reveals that the global minimum is not a deepest one, since there are two other local minima GA5 and GA6 on either side of the global minimum with an energy of about 0.95 and 0.97 kcal/mol, respectively, which causes the broadening of the potential well. The conformers GA5, GA6 and GA7 are not the stable ones since they get annihilated during the optimization and have damped into the global one.
ISSN:0166-1280
1872-7999
DOI:10.1016/S0166-1280(02)00467-0