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 language | English |
|---|---|
| Pages (from-to) | 41-52 |
| Number of pages | 12 |
| Journal | Journal of Molecular Structure: THEOCHEM |
| Volume | 395-396 |
| Issue number | 1-3 |
| Publication status | Published - máj. 26 1997 |
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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
}
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 -