Structures of inclusion complexes of halogenbenzoic acids and α-cyclodextrin based on AM1 calculations

Martin Pumera, Lubomír Rulíšek

Research output: Contribution to journalArticle

18 Citations (Scopus)

Abstract

Semi-empirical quantum mechanics calculations using AM1 (Austin Method 1) were carried out for various host-guest combinations of α-cyclodextrin and mono-halogen benzoic acids. The energetically favorable inclusion structures were identified. The AM1 results show that α-cyclodextrin complexes with mono-halogen benzoic acid acids (where the halogen is chlorine, bromide, iodine) as guest compounds are more stable in the "head first" position than in the "tail-first" position for meta and para isomers while ortho mono-halogen benzoic acids complexes with α-cyclodextrin are more stable in "tail-first" position. The calculated structures were found to be in good agreement with those obtained from crystalographic databases.

Original languageEnglish
Pages (from-to)799-803
Number of pages5
JournalJournal of Molecular Modeling
Volume12
Issue number6
DOIs
Publication statusPublished - 2006 Sep 1

Fingerprint

Halogens
Benzoic acid
Cyclodextrins
halogens
benzoic acid
inclusions
acids
Acids
Benzoates
Quantum theory
Iodine
Isomers
Chlorine
Benzoic Acid
iodine
chlorine
quantum mechanics
bromides
isomers
austin

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Computer Science Applications
  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Computational Theory and Mathematics
  • Inorganic Chemistry

Cite this

@article{3ba2effc449541028ad5da61c9acdd48,
title = "Structures of inclusion complexes of halogenbenzoic acids and α-cyclodextrin based on AM1 calculations",
abstract = "Semi-empirical quantum mechanics calculations using AM1 (Austin Method 1) were carried out for various host-guest combinations of α-cyclodextrin and mono-halogen benzoic acids. The energetically favorable inclusion structures were identified. The AM1 results show that α-cyclodextrin complexes with mono-halogen benzoic acid acids (where the halogen is chlorine, bromide, iodine) as guest compounds are more stable in the {"}head first{"} position than in the {"}tail-first{"} position for meta and para isomers while ortho mono-halogen benzoic acids complexes with α-cyclodextrin are more stable in {"}tail-first{"} position. The calculated structures were found to be in good agreement with those obtained from crystalographic databases.",
author = "Martin Pumera and Lubom{\'i}r Rul{\'i}šek",
year = "2006",
month = "9",
day = "1",
doi = "10.1007/s00894-005-0082-y",
language = "English",
volume = "12",
pages = "799--803",
journal = "Journal of Molecular Modeling",
issn = "1610-2940",
publisher = "Springer Verlag",
number = "6",

}

Structures of inclusion complexes of halogenbenzoic acids and α-cyclodextrin based on AM1 calculations. / Pumera, Martin; Rulíšek, Lubomír.

In: Journal of Molecular Modeling, Vol. 12, No. 6, 01.09.2006, p. 799-803.

Research output: Contribution to journalArticle

TY - JOUR

T1 - Structures of inclusion complexes of halogenbenzoic acids and α-cyclodextrin based on AM1 calculations

AU - Pumera, Martin

AU - Rulíšek, Lubomír

PY - 2006/9/1

Y1 - 2006/9/1

N2 - Semi-empirical quantum mechanics calculations using AM1 (Austin Method 1) were carried out for various host-guest combinations of α-cyclodextrin and mono-halogen benzoic acids. The energetically favorable inclusion structures were identified. The AM1 results show that α-cyclodextrin complexes with mono-halogen benzoic acid acids (where the halogen is chlorine, bromide, iodine) as guest compounds are more stable in the "head first" position than in the "tail-first" position for meta and para isomers while ortho mono-halogen benzoic acids complexes with α-cyclodextrin are more stable in "tail-first" position. The calculated structures were found to be in good agreement with those obtained from crystalographic databases.

AB - Semi-empirical quantum mechanics calculations using AM1 (Austin Method 1) were carried out for various host-guest combinations of α-cyclodextrin and mono-halogen benzoic acids. The energetically favorable inclusion structures were identified. The AM1 results show that α-cyclodextrin complexes with mono-halogen benzoic acid acids (where the halogen is chlorine, bromide, iodine) as guest compounds are more stable in the "head first" position than in the "tail-first" position for meta and para isomers while ortho mono-halogen benzoic acids complexes with α-cyclodextrin are more stable in "tail-first" position. The calculated structures were found to be in good agreement with those obtained from crystalographic databases.

UR - http://www.scopus.com/inward/record.url?scp=33749245828&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=33749245828&partnerID=8YFLogxK

U2 - 10.1007/s00894-005-0082-y

DO - 10.1007/s00894-005-0082-y

M3 - Article

C2 - 16496193

AN - SCOPUS:33749245828

VL - 12

SP - 799

EP - 803

JO - Journal of Molecular Modeling

JF - Journal of Molecular Modeling

SN - 1610-2940

IS - 6

ER -