Quantum chemical studies on the partial hydrogenolysis of methyl 2,3-O-diphenylmethylene-α-L-rhamnopyranoside

Attila Mándi, I. Komáromi, A. Borbás, Dezso Szikra, István P. Nagy, A. Lipták, S. Antus

Research output: Article

2 Citations (Scopus)

Abstract

The potential energy surface for dioxolane ring-opening and hydride donation for the title compound has been mapped. The transition state (TS) was determined at various levels of theories and it has been proven by intrinsic reaction coordinate calculations that it connects the reactant to the product. The breaking of the O3-Cacetal bond and formation of the new H-C bond seems to occur in one (rate limiting) elementary step, which is, however, rather asynchronous.

Original languageEnglish
Pages (from-to)1256-1259
Number of pages4
JournalTetrahedron Letters
Volume52
Issue number12
DOIs
Publication statusPublished - márc. 23 2011

Fingerprint

Potential energy surfaces
Hydrogenolysis
Hydrides
formal glycol

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Quantum chemical studies on the partial hydrogenolysis of methyl 2,3-O-diphenylmethylene-α-L-rhamnopyranoside. / Mándi, Attila; Komáromi, I.; Borbás, A.; Szikra, Dezso; Nagy, István P.; Lipták, A.; Antus, S.

In: Tetrahedron Letters, Vol. 52, No. 12, 23.03.2011, p. 1256-1259.

Research output: Article

@article{b21ee76649124d32a4267e0e51dd551a,
title = "Quantum chemical studies on the partial hydrogenolysis of methyl 2,3-O-diphenylmethylene-α-L-rhamnopyranoside",
abstract = "The potential energy surface for dioxolane ring-opening and hydride donation for the title compound has been mapped. The transition state (TS) was determined at various levels of theories and it has been proven by intrinsic reaction coordinate calculations that it connects the reactant to the product. The breaking of the O3-Cacetal bond and formation of the new H-C bond seems to occur in one (rate limiting) elementary step, which is, however, rather asynchronous.",
keywords = "Chloroalane, Diphenylmethylene acetal, Mechanistic study, Partial hydrogenolysis, Quantum chemistry",
author = "Attila M{\'a}ndi and I. Kom{\'a}romi and A. Borb{\'a}s and Dezso Szikra and Nagy, {Istv{\'a}n P.} and A. Lipt{\'a}k and S. Antus",
year = "2011",
month = "3",
day = "23",
doi = "10.1016/j.tetlet.2011.01.021",
language = "English",
volume = "52",
pages = "1256--1259",
journal = "Tetrahedron Letters",
issn = "0040-4039",
publisher = "Elsevier Limited",
number = "12",

}

TY - JOUR

T1 - Quantum chemical studies on the partial hydrogenolysis of methyl 2,3-O-diphenylmethylene-α-L-rhamnopyranoside

AU - Mándi, Attila

AU - Komáromi, I.

AU - Borbás, A.

AU - Szikra, Dezso

AU - Nagy, István P.

AU - Lipták, A.

AU - Antus, S.

PY - 2011/3/23

Y1 - 2011/3/23

N2 - The potential energy surface for dioxolane ring-opening and hydride donation for the title compound has been mapped. The transition state (TS) was determined at various levels of theories and it has been proven by intrinsic reaction coordinate calculations that it connects the reactant to the product. The breaking of the O3-Cacetal bond and formation of the new H-C bond seems to occur in one (rate limiting) elementary step, which is, however, rather asynchronous.

AB - The potential energy surface for dioxolane ring-opening and hydride donation for the title compound has been mapped. The transition state (TS) was determined at various levels of theories and it has been proven by intrinsic reaction coordinate calculations that it connects the reactant to the product. The breaking of the O3-Cacetal bond and formation of the new H-C bond seems to occur in one (rate limiting) elementary step, which is, however, rather asynchronous.

KW - Chloroalane

KW - Diphenylmethylene acetal

KW - Mechanistic study

KW - Partial hydrogenolysis

KW - Quantum chemistry

UR - http://www.scopus.com/inward/record.url?scp=79951755052&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=79951755052&partnerID=8YFLogxK

U2 - 10.1016/j.tetlet.2011.01.021

DO - 10.1016/j.tetlet.2011.01.021

M3 - Article

AN - SCOPUS:79951755052

VL - 52

SP - 1256

EP - 1259

JO - Tetrahedron Letters

JF - Tetrahedron Letters

SN - 0040-4039

IS - 12

ER -