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2‐Amino‐2‐Oxazolines, Part VIII. Calculated Molecular Properties of Tautomeric Species
Author(s) -
Ouhabi Jamal,
Jarry Christian,
Zouanate Abdelhadi,
Carpy Alain
Publication year - 1997
Publication title -
archiv der pharmazie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.468
H-Index - 61
eISSN - 1521-4184
pISSN - 0365-6233
DOI - 10.1002/ardp.19973301202
Subject(s) - tautomer , mndo , chemistry , ab initio , computational chemistry , ab initio quantum chemistry methods , protonation , stereochemistry , molecule , organic chemistry , ion
The geometries, tautomerization energies, and dipole moments of the tautomeric species of the 2‐amino‐2‐oxazoline heterocycle were calculated with full geometry optimization using semiempirical (MNDO, AM1 and PM3) and ab initio (RHF/6–31G) methods. The planar conformation of the amino form is well reproduced by the semiempirical and by the ab initio methods as compared with X‐ray structures in which this form is found. However the exocyclic nitrogen atom is pyramidalized in the semiempirical geometries whereas the ab initio method reproduces a sp 2 hybridization state. The twisted conformation of the imino form is better reproduced by the ab initio calculation. All methods (semiempirical and ab initio ) show a stability energy value in favour of the amino tautomer of the neutral heterocycle. On the contrary, the dominant species of the charged heterocycle is the imino tautomer, protonated on the exocyclic nitrogen atom. Molecular electrostatic potential calculations confirmed this tendency. Finally the 3D‐lipophilicity profile of the heterocycle completed the investigation of the tautomerism.