Abstract
The molecular geometry of benzalazine derivatives was studied by spectroscopic and semiempirical MO (MNDO, CNDO/2) methods. The existence of a strong intramolecular H-bond (7-10 kcal mol-1) was determined by 1H NMR spectroscopy in molecules having a hydroxy group in the ortho position with reference to the diazine central bridge. A study of the H-bonds using the MNDO method proved to be unsatisfactory, whereas the results obtained by the CNDO/2 method were in excellent agreement with experimental values. Both theoretical calculations (CNDO/2) and experimental evidence (UV and 1H NMR) show that the existence of a first H-bond weakened the force of a second in benzalazines. © 1987.
Original language | English |
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Pages (from-to) | 1-15 |
Journal | Journal of Molecular Structure: THEOCHEM |
Volume | 150 |
Issue number | 1-2 |
DOIs | |
Publication status | Published - 1 Jan 1987 |