Structural studies of mesogen benzalazine derivatives. Part I. Semiempirical MO calculations (CNDO/2,MNDO) on intramolecular H-bond and vicinal interactions

Jose Elguero; Carlos Jaime; Mercedes Marcos; Enrique Melendez; Francisco Sanchez-Ferrando; Jose Luis Serrano

doi:10.1016/0166-1280(87)80021-0

Structural studies of mesogen benzalazine derivatives. Part I. Semiempirical MO calculations (CNDO/2,MNDO) on intramolecular H-bond and vicinal interactions

Jose Elguero, Carlos Jaime, Mercedes Marcos, Enrique Melendez, Francisco Sanchez-Ferrando, Jose Luis Serrano

Department of Chemistry

Research output: Contribution to journal › Article › Research › peer-review

20 Citations (Scopus)

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
Pages (from-to)	1-15
Journal	Journal of Molecular Structure: THEOCHEM
Volume	150
Issue number	1-2
DOIs	https://doi.org/10.1016/0166-1280(87)80021-0
Publication status	Published - 1 Jan 1987

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@article{1bf4e3d4f0c04c0fa3883f9d3aeb1c2d,

title = "Structural studies of mesogen benzalazine derivatives. Part I. Semiempirical MO calculations (CNDO/2,MNDO) on intramolecular H-bond and vicinal interactions",

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. {\textcopyright} 1987.",

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Structural studies of mesogen benzalazine derivatives. Part I. Semiempirical MO calculations (CNDO/2,MNDO) on intramolecular H-bond and vicinal interactions. / Elguero, Jose; Jaime, Carlos; Marcos, Mercedes; Melendez, Enrique; Sanchez-Ferrando, Francisco; Serrano, Jose Luis.

In: Journal of Molecular Structure: THEOCHEM, Vol. 150, No. 1-2, 01.01.1987, p. 1-15.

Research output: Contribution to journal › Article › Research › peer-review

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

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AU - Melendez, Enrique

AU - Sanchez-Ferrando, Francisco

AU - Serrano, Jose Luis

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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.

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