Exploratory molecular orbital calculations on the keto and enol forms of selected antifungals and those of side-chain substituted acetophenone model compounds

A. M. Rodríguez, F. A. Giannini, H. A. Baldoni, F. D. Suvire, S. Zacchino, R. D. Enriz, P. Csaszar, I. Csizmadia

Research output: Contribution to journalArticle

15 Citations (Scopus)

Abstract

Conformational potential energy surfaces were generated using the semiempirical AM1 method for selected α-substituted arylpropanoids. The global minima were subjected to full AM1 geometry optimizations, Keto-enol tautomerization energies were also computed at the AM1 level. The results obtained were compared to those of Simple Huckel Molecular Orbital calculations. Antifungal activities of the compounds studied were reported as minimal inhibitory concentration values. These values were correlated with computed molecular parameters. A set of α-substituted acetophenones (using Me, F and Cl as substituents) were also studied, as model compounds for the antifungals, at the AM1 and the RHF/STO-3G levels of theory. The enolization energies were calculated at both levels of theory.

Original languageEnglish
Pages (from-to)283-303
Number of pages21
JournalJournal of Molecular Structure: THEOCHEM
Volume463
Issue number3
DOIs
Publication statusPublished - May 3 1999

Fingerprint

Acetophenones
Orbital calculations
Potential energy surfaces
Molecular orbitals
molecular orbitals
Geometry
potential energy
optimization
energy
geometry
acetophenone

Keywords

  • α-substituted acetophenones
  • Antifungal activity
  • Conformational analysis
  • Keto-enol tautomerization
  • Potential energy surfaces
  • Semiempirical and ab initio computations

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Computational Theory and Mathematics
  • Atomic and Molecular Physics, and Optics

Cite this

Exploratory molecular orbital calculations on the keto and enol forms of selected antifungals and those of side-chain substituted acetophenone model compounds. / Rodríguez, A. M.; Giannini, F. A.; Baldoni, H. A.; Suvire, F. D.; Zacchino, S.; Enriz, R. D.; Csaszar, P.; Csizmadia, I.

In: Journal of Molecular Structure: THEOCHEM, Vol. 463, No. 3, 03.05.1999, p. 283-303.

Research output: Contribution to journalArticle

Rodríguez, A. M. ; Giannini, F. A. ; Baldoni, H. A. ; Suvire, F. D. ; Zacchino, S. ; Enriz, R. D. ; Csaszar, P. ; Csizmadia, I. / Exploratory molecular orbital calculations on the keto and enol forms of selected antifungals and those of side-chain substituted acetophenone model compounds. In: Journal of Molecular Structure: THEOCHEM. 1999 ; Vol. 463, No. 3. pp. 283-303.
@article{3373e0831267474b979362b8a3b6f38e,
title = "Exploratory molecular orbital calculations on the keto and enol forms of selected antifungals and those of side-chain substituted acetophenone model compounds",
abstract = "Conformational potential energy surfaces were generated using the semiempirical AM1 method for selected α-substituted arylpropanoids. The global minima were subjected to full AM1 geometry optimizations, Keto-enol tautomerization energies were also computed at the AM1 level. The results obtained were compared to those of Simple Huckel Molecular Orbital calculations. Antifungal activities of the compounds studied were reported as minimal inhibitory concentration values. These values were correlated with computed molecular parameters. A set of α-substituted acetophenones (using Me, F and Cl as substituents) were also studied, as model compounds for the antifungals, at the AM1 and the RHF/STO-3G levels of theory. The enolization energies were calculated at both levels of theory.",
keywords = "α-substituted acetophenones, Antifungal activity, Conformational analysis, Keto-enol tautomerization, Potential energy surfaces, Semiempirical and ab initio computations",
author = "Rodr{\'i}guez, {A. M.} and Giannini, {F. A.} and Baldoni, {H. A.} and Suvire, {F. D.} and S. Zacchino and Enriz, {R. D.} and P. Csaszar and I. Csizmadia",
year = "1999",
month = "5",
day = "3",
doi = "10.1016/S0166-1280(98)00572-7",
language = "English",
volume = "463",
pages = "283--303",
journal = "Computational and Theoretical Chemistry",
issn = "2210-271X",
publisher = "Elsevier BV",
number = "3",

}

TY - JOUR

T1 - Exploratory molecular orbital calculations on the keto and enol forms of selected antifungals and those of side-chain substituted acetophenone model compounds

AU - Rodríguez, A. M.

AU - Giannini, F. A.

AU - Baldoni, H. A.

AU - Suvire, F. D.

AU - Zacchino, S.

AU - Enriz, R. D.

AU - Csaszar, P.

AU - Csizmadia, I.

PY - 1999/5/3

Y1 - 1999/5/3

N2 - Conformational potential energy surfaces were generated using the semiempirical AM1 method for selected α-substituted arylpropanoids. The global minima were subjected to full AM1 geometry optimizations, Keto-enol tautomerization energies were also computed at the AM1 level. The results obtained were compared to those of Simple Huckel Molecular Orbital calculations. Antifungal activities of the compounds studied were reported as minimal inhibitory concentration values. These values were correlated with computed molecular parameters. A set of α-substituted acetophenones (using Me, F and Cl as substituents) were also studied, as model compounds for the antifungals, at the AM1 and the RHF/STO-3G levels of theory. The enolization energies were calculated at both levels of theory.

AB - Conformational potential energy surfaces were generated using the semiempirical AM1 method for selected α-substituted arylpropanoids. The global minima were subjected to full AM1 geometry optimizations, Keto-enol tautomerization energies were also computed at the AM1 level. The results obtained were compared to those of Simple Huckel Molecular Orbital calculations. Antifungal activities of the compounds studied were reported as minimal inhibitory concentration values. These values were correlated with computed molecular parameters. A set of α-substituted acetophenones (using Me, F and Cl as substituents) were also studied, as model compounds for the antifungals, at the AM1 and the RHF/STO-3G levels of theory. The enolization energies were calculated at both levels of theory.

KW - α-substituted acetophenones

KW - Antifungal activity

KW - Conformational analysis

KW - Keto-enol tautomerization

KW - Potential energy surfaces

KW - Semiempirical and ab initio computations

UR - http://www.scopus.com/inward/record.url?scp=0343250323&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0343250323&partnerID=8YFLogxK

U2 - 10.1016/S0166-1280(98)00572-7

DO - 10.1016/S0166-1280(98)00572-7

M3 - Article

VL - 463

SP - 283

EP - 303

JO - Computational and Theoretical Chemistry

JF - Computational and Theoretical Chemistry

SN - 2210-271X

IS - 3

ER -