Intramolecular hydrogen bonding in primary hydroxyl of thymine 1-(1-Deoxy-β-D-Psicofuranosyl) nucleoside

Xavier Martin; Miquel Moreno; José M. Lluch; Annie Grouiller

doi:10.1016/S0040-4020(01)89697-6

Intramolecular hydrogen bonding in primary hydroxyl of thymine 1-(1-Deoxy-β-D-Psicofuranosyl) nucleoside

Xavier Martin, Miquel Moreno, José M. Lluch, Annie Grouiller

Research output: Contribution to journal › Article › Research › peer-review

5 Citations (Scopus)

Abstract

A conformational analysis of 1-(1-Deoxy-β-D-Psicorofuranosyl) thymine (1) and 1-(β-D-Ribofuranosyl) thymine (2) has been performed by using the semiempirical AM1 methodology. A topological analysis of the total charge density and the Laplacian of both molecules is carried out in order to assess the presence of an intramolecular hydrogen bond. It is concluded that a clear hydrogen bond exists in structure (1) in such a way that the primary alcohol is experimentally found totally unreactive with any reagent in any condition. © 1994.

Original language	English
Pages (from-to)	6689-6694
Journal	Tetrahedron
Volume	50
Issue number	22
DOIs	https://doi.org/10.1016/S0040-4020(01)89697-6
Publication status	Published - 1 Jan 1994

Keywords

AM1 semiempirical method.
Charge density topological analysis
Conformational analysis of thymine 1-(1-Deoxy-β-D-Psicorofuranosyl) nucleoside
Intramolecular hydrogen bond
Laplacian of the charge density

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@article{f72b545b96a545f685b03ce991ecdf35,

title = "Intramolecular hydrogen bonding in primary hydroxyl of thymine 1-(1-Deoxy-β-D-Psicofuranosyl) nucleoside",

abstract = "A conformational analysis of 1-(1-Deoxy-β-D-Psicorofuranosyl) thymine (1) and 1-(β-D-Ribofuranosyl) thymine (2) has been performed by using the semiempirical AM1 methodology. A topological analysis of the total charge density and the Laplacian of both molecules is carried out in order to assess the presence of an intramolecular hydrogen bond. It is concluded that a clear hydrogen bond exists in structure (1) in such a way that the primary alcohol is experimentally found totally unreactive with any reagent in any condition. {\textcopyright} 1994.",

keywords = "AM1 semiempirical method., Charge density topological analysis, Conformational analysis of thymine 1-(1-Deoxy-β-D-Psicorofuranosyl) nucleoside, Intramolecular hydrogen bond, Laplacian of the charge density",

author = "Xavier Martin and Miquel Moreno and Lluch, {Jos{\'e} M.} and Annie Grouiller",

year = "1994",

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doi = "10.1016/S0040-4020(01)89697-6",

language = "English",

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T1 - Intramolecular hydrogen bonding in primary hydroxyl of thymine 1-(1-Deoxy-β-D-Psicofuranosyl) nucleoside

AU - Martin, Xavier

AU - Moreno, Miquel

AU - Lluch, José M.

AU - Grouiller, Annie

PY - 1994/1/1

Y1 - 1994/1/1

N2 - A conformational analysis of 1-(1-Deoxy-β-D-Psicorofuranosyl) thymine (1) and 1-(β-D-Ribofuranosyl) thymine (2) has been performed by using the semiempirical AM1 methodology. A topological analysis of the total charge density and the Laplacian of both molecules is carried out in order to assess the presence of an intramolecular hydrogen bond. It is concluded that a clear hydrogen bond exists in structure (1) in such a way that the primary alcohol is experimentally found totally unreactive with any reagent in any condition. © 1994.

AB - A conformational analysis of 1-(1-Deoxy-β-D-Psicorofuranosyl) thymine (1) and 1-(β-D-Ribofuranosyl) thymine (2) has been performed by using the semiempirical AM1 methodology. A topological analysis of the total charge density and the Laplacian of both molecules is carried out in order to assess the presence of an intramolecular hydrogen bond. It is concluded that a clear hydrogen bond exists in structure (1) in such a way that the primary alcohol is experimentally found totally unreactive with any reagent in any condition. © 1994.

KW - AM1 semiempirical method.

KW - Charge density topological analysis

KW - Conformational analysis of thymine 1-(1-Deoxy-β-D-Psicorofuranosyl) nucleoside

KW - Intramolecular hydrogen bond

KW - Laplacian of the charge density

U2 - 10.1016/S0040-4020(01)89697-6

DO - 10.1016/S0040-4020(01)89697-6

M3 - Article

VL - 50

SP - 6689

EP - 6694

JO - Tetrahedron

JF - Tetrahedron

SN - 0040-4020

IS - 22

ER -