An ab initio study on selected models of 1,2-cis-and 1,2-trans-cyclic carbamates of glucopyranosyl amine

B. Paizs, I. Pintér, J. Kovács, W. Viviani, A. Marsura, P. Friant-Michel, I. Csizmadia

Research output: Article

7 Citations (Scopus)

Abstract

Total energies of various conformations of trans-and cis-isomers of 2-amino-cyclohexanol (5) and those of 2-amino-3-hydroxy-tetrahydropyrane (6) as well as those of 2,3-cyclic carbamates of 2-amino-3-hydroxy-tetrahydropyrane (7) were computed at HF/6-31G and HF/6-31G** level of theory for modelling the energy differences between trans-and cis-1,2-cyclic carbamates of gluco-and xylopyranosyl amine (1,2 and 3,4, respectively). In the case of the chair forms of both 5 and 6, the trans isomers were found to be more stable than the cis ones. The stability of the different structures was also governed by the internal hydrogen bonds involving NH2 and OH groups, as well as the ring oxygen atom. In the case of 7, the formation of the oxazolinone ring results in decreasing the total energy of the cis isomer with respect to the trans compound. Using appropriate isodesmic reaction equations, stabilization energies were calculated for all of the model structures of 5-7, as well as for the transition from cyclohexane to tetrahydropyrane. The energy values indicated that the introduction of the ring oxygen causes stabilization in all cases.

Original languageEnglish
Pages (from-to)41-52
Number of pages12
JournalJournal of Molecular Structure: THEOCHEM
Volume395-396
Issue number1-3
Publication statusPublished - máj. 26 1997

Fingerprint

Carbamates
Isomers
Amines
amines
Cyclohexanols
Oxygen
Stabilization
isomers
Hydrogen
Cyclohexane
Model structures
rings
stabilization
Conformations
energy
Hydrogen bonds
Atoms
cyclohexane
seats
oxygen atoms

ASJC Scopus subject areas

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

Cite this

An ab initio study on selected models of 1,2-cis-and 1,2-trans-cyclic carbamates of glucopyranosyl amine. / Paizs, B.; Pintér, I.; Kovács, J.; Viviani, W.; Marsura, A.; Friant-Michel, P.; Csizmadia, I.

In: Journal of Molecular Structure: THEOCHEM, Vol. 395-396, No. 1-3, 26.05.1997, p. 41-52.

Research output: Article

@article{cedbe6bea3ab47f2a2f214af9c58a26a,
title = "An ab initio study on selected models of 1,2-cis-and 1,2-trans-cyclic carbamates of glucopyranosyl amine",
abstract = "Total energies of various conformations of trans-and cis-isomers of 2-amino-cyclohexanol (5) and those of 2-amino-3-hydroxy-tetrahydropyrane (6) as well as those of 2,3-cyclic carbamates of 2-amino-3-hydroxy-tetrahydropyrane (7) were computed at HF/6-31G and HF/6-31G** level of theory for modelling the energy differences between trans-and cis-1,2-cyclic carbamates of gluco-and xylopyranosyl amine (1,2 and 3,4, respectively). In the case of the chair forms of both 5 and 6, the trans isomers were found to be more stable than the cis ones. The stability of the different structures was also governed by the internal hydrogen bonds involving NH2 and OH groups, as well as the ring oxygen atom. In the case of 7, the formation of the oxazolinone ring results in decreasing the total energy of the cis isomer with respect to the trans compound. Using appropriate isodesmic reaction equations, stabilization energies were calculated for all of the model structures of 5-7, as well as for the transition from cyclohexane to tetrahydropyrane. The energy values indicated that the introduction of the ring oxygen causes stabilization in all cases.",
keywords = "Ab initio, Amino-cyclohexanol, Amino-tetrahydorpyrane, Configurational stability, Conformational stability, Cyclic carbamate, Glycopyranosyl amine",
author = "B. Paizs and I. Pint{\'e}r and J. Kov{\'a}cs and W. Viviani and A. Marsura and P. Friant-Michel and I. Csizmadia",
year = "1997",
month = "5",
day = "26",
language = "English",
volume = "395-396",
pages = "41--52",
journal = "Computational and Theoretical Chemistry",
issn = "2210-271X",
publisher = "Elsevier BV",
number = "1-3",

}

TY - JOUR

T1 - An ab initio study on selected models of 1,2-cis-and 1,2-trans-cyclic carbamates of glucopyranosyl amine

AU - Paizs, B.

AU - Pintér, I.

AU - Kovács, J.

AU - Viviani, W.

AU - Marsura, A.

AU - Friant-Michel, P.

AU - Csizmadia, I.

PY - 1997/5/26

Y1 - 1997/5/26

N2 - Total energies of various conformations of trans-and cis-isomers of 2-amino-cyclohexanol (5) and those of 2-amino-3-hydroxy-tetrahydropyrane (6) as well as those of 2,3-cyclic carbamates of 2-amino-3-hydroxy-tetrahydropyrane (7) were computed at HF/6-31G and HF/6-31G** level of theory for modelling the energy differences between trans-and cis-1,2-cyclic carbamates of gluco-and xylopyranosyl amine (1,2 and 3,4, respectively). In the case of the chair forms of both 5 and 6, the trans isomers were found to be more stable than the cis ones. The stability of the different structures was also governed by the internal hydrogen bonds involving NH2 and OH groups, as well as the ring oxygen atom. In the case of 7, the formation of the oxazolinone ring results in decreasing the total energy of the cis isomer with respect to the trans compound. Using appropriate isodesmic reaction equations, stabilization energies were calculated for all of the model structures of 5-7, as well as for the transition from cyclohexane to tetrahydropyrane. The energy values indicated that the introduction of the ring oxygen causes stabilization in all cases.

AB - Total energies of various conformations of trans-and cis-isomers of 2-amino-cyclohexanol (5) and those of 2-amino-3-hydroxy-tetrahydropyrane (6) as well as those of 2,3-cyclic carbamates of 2-amino-3-hydroxy-tetrahydropyrane (7) were computed at HF/6-31G and HF/6-31G** level of theory for modelling the energy differences between trans-and cis-1,2-cyclic carbamates of gluco-and xylopyranosyl amine (1,2 and 3,4, respectively). In the case of the chair forms of both 5 and 6, the trans isomers were found to be more stable than the cis ones. The stability of the different structures was also governed by the internal hydrogen bonds involving NH2 and OH groups, as well as the ring oxygen atom. In the case of 7, the formation of the oxazolinone ring results in decreasing the total energy of the cis isomer with respect to the trans compound. Using appropriate isodesmic reaction equations, stabilization energies were calculated for all of the model structures of 5-7, as well as for the transition from cyclohexane to tetrahydropyrane. The energy values indicated that the introduction of the ring oxygen causes stabilization in all cases.

KW - Ab initio

KW - Amino-cyclohexanol

KW - Amino-tetrahydorpyrane

KW - Configurational stability

KW - Conformational stability

KW - Cyclic carbamate

KW - Glycopyranosyl amine

UR - http://www.scopus.com/inward/record.url?scp=0039380159&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0039380159&partnerID=8YFLogxK

M3 - Article

AN - SCOPUS:0039380159

VL - 395-396

SP - 41

EP - 52

JO - Computational and Theoretical Chemistry

JF - Computational and Theoretical Chemistry

SN - 2210-271X

IS - 1-3

ER -