TY - JOUR
T1 - Structural studies of mesogen benzalazine derivatives. Part I. Semiempirical MO calculations (CNDO/2,MNDO) on intramolecular H-bond and vicinal interactions
AU - Elguero, Jose
AU - Jaime, Carlos
AU - Marcos, Mercedes
AU - Melendez, Enrique
AU - Sanchez-Ferrando, Francisco
AU - Serrano, Jose Luis
PY - 1987/1/1
Y1 - 1987/1/1
N2 - 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.
AB - 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.
U2 - 10.1016/0166-1280(87)80021-0
DO - 10.1016/0166-1280(87)80021-0
M3 - Article
SN - 0166-1280
VL - 150
SP - 1
EP - 15
JO - Journal of Molecular Structure: THEOCHEM
JF - Journal of Molecular Structure: THEOCHEM
IS - 1-2
ER -