A search for C-H···O type hydrogen bonds in Lamivudine (3TC). An exploratory conformational and electronic analysis

Autores
Fidanza, N. G.; Suvire, Fernando Daniel; Sosa, Gladis Laura; Lobayan, Rosana Maria; Enriz, Ricardo Daniel; Peruchena, Nelida Maria
Año de publicación
2001
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
A conformational study of the molecule Lamivudine (3TC), or cis-1-[2′-hydroxymethyl-5′-(1,3-oxathiolanyl)] cytosine, was carried out. Rotation about the C-N bond (φ1) and about the C-CH2(OH) bond (φ2), which connects the hydroxymethyl group to the five member ring, led to a conformational potential energy surface. The conformational potential energy 2D map, obtained at the HF/3-21G level of theory, had several minima. A topological analysis of the electron density was carried out on four selected ab initio minimum energy conformations, using judiciously constructed hartree-fock (RHF) wave functions. In order to see all possible hydrogen bonding, the DFT wave function was generated using a mixed basis set; a 6-311 + +G** basis was employed on atoms involved in hydrogen bonding interactions and a 3-21G basis on all other atoms. For this analysis the theory of atoms in molecules, developed by Bader, was used. The stability of the intramolecular hydrogen bonding interactions was analyzed in terms of the results obtained.
Fil: Fidanza, N. G.. Universidad Nacional del Nordeste. Facultad de Ciencias Exactas Naturales y Agrimensura. Departamento de Química; Argentina
Fil: Suvire, Fernando Daniel. Universidad Nacional de San Luis. Facultad de Química, Bioquímica y Farmacia. Departamento de Química; Argentina
Fil: Sosa, Gladis Laura. Universidad Nacional del Nordeste. Facultad de Ciencias Exactas Naturales y Agrimensura. Departamento de Química; Argentina
Fil: Lobayan, Rosana Maria. Universidad Nacional del Nordeste. Facultad de Ciencias Exactas Naturales y Agrimensura. Departamento de Química; Argentina
Fil: Enriz, Ricardo Daniel. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - San Luis. Instituto Multidisciplinario de Investigaciones Biológicas de San Luis. Universidad Nacional de San Luis. Facultad de Ciencias Físico Matemáticas y Naturales. Instituto Multidisciplinario de Investigaciones Biológicas de San Luis; Argentina
Fil: Peruchena, Nelida Maria. Universidad Nacional del Nordeste. Facultad de Ciencias Exactas Naturales y Agrimensura. Departamento de Química; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Nordeste; Argentina
Materia
AB INITIO
ATOMS IN MOLECULES (AIM)
CONFORMATIONAL ANALYSIS
DENSITY FUNCTIONAL THEORY (DFT)
HF
HYDROGEN BOND
TOPOLOGICAL ANALYSIS OF ELECTRON DENSITY
Nivel de accesibilidad
acceso abierto
Condiciones de uso
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
Repositorio
CONICET Digital (CONICET)
Institución
Consejo Nacional de Investigaciones Científicas y Técnicas
OAI Identificador
oai:ri.conicet.gov.ar:11336/134666
Acceder
id CONICETDig_059d93afbe37d30aac49a54a2fcce373
oai_identifier_str oai:ri.conicet.gov.ar:11336/134666
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling A search for C-H···O type hydrogen bonds in Lamivudine (3TC). An exploratory conformational and electronic analysisFidanza, N. G.Suvire, Fernando DanielSosa, Gladis LauraLobayan, Rosana MariaEnriz, Ricardo DanielPeruchena, Nelida MariaAB INITIOATOMS IN MOLECULES (AIM)CONFORMATIONAL ANALYSISDENSITY FUNCTIONAL THEORY (DFT)HFHYDROGEN BONDTOPOLOGICAL ANALYSIS OF ELECTRON DENSITYhttps://purl.org/becyt/ford/1.3https://purl.org/becyt/ford/1A conformational study of the molecule Lamivudine (3TC), or cis-1-[2′-hydroxymethyl-5′-(1,3-oxathiolanyl)] cytosine, was carried out. Rotation about the C-N bond (φ1) and about the C-CH2(OH) bond (φ2), which connects the hydroxymethyl group to the five member ring, led to a conformational potential energy surface. The conformational potential energy 2D map, obtained at the HF/3-21G level of theory, had several minima. A topological analysis of the electron density was carried out on four selected ab initio minimum energy conformations, using judiciously constructed hartree-fock (RHF) wave functions. In order to see all possible hydrogen bonding, the DFT wave function was generated using a mixed basis set; a 6-311 + +G** basis was employed on atoms involved in hydrogen bonding interactions and a 3-21G basis on all other atoms. For this analysis the theory of atoms in molecules, developed by Bader, was used. The stability of the intramolecular hydrogen bonding interactions was analyzed in terms of the results obtained.Fil: Fidanza, N. G.. Universidad Nacional del Nordeste. Facultad de Ciencias Exactas Naturales y Agrimensura. Departamento de Química; ArgentinaFil: Suvire, Fernando Daniel. Universidad Nacional de San Luis. Facultad de Química, Bioquímica y Farmacia. Departamento de Química; ArgentinaFil: Sosa, Gladis Laura. Universidad Nacional del Nordeste. Facultad de Ciencias Exactas Naturales y Agrimensura. Departamento de Química; ArgentinaFil: Lobayan, Rosana Maria. Universidad Nacional del Nordeste. Facultad de Ciencias Exactas Naturales y Agrimensura. Departamento de Química; ArgentinaFil: Enriz, Ricardo Daniel. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - San Luis. Instituto Multidisciplinario de Investigaciones Biológicas de San Luis. Universidad Nacional de San Luis. Facultad de Ciencias Físico Matemáticas y Naturales. Instituto Multidisciplinario de Investigaciones Biológicas de San Luis; ArgentinaFil: Peruchena, Nelida Maria. Universidad Nacional del Nordeste. Facultad de Ciencias Exactas Naturales y Agrimensura. Departamento de Química; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Nordeste; ArgentinaElsevier Science2001-06-22info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfapplication/pdfapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/134666Fidanza, N. G.; Suvire, Fernando Daniel; Sosa, Gladis Laura; Lobayan, Rosana Maria; Enriz, Ricardo Daniel; et al.; A search for C-H···O type hydrogen bonds in Lamivudine (3TC). An exploratory conformational and electronic analysis; Elsevier Science; Journal of Molecular Structure Theochem; 543; 1-3; 22-6-2001; 185-1930166-1280CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/url/https://www.sciencedirect.com/science/article/abs/pii/S0166128001003463info:eu-repo/semantics/altIdentifier/doi/10.1016/S0166-1280(01)00346-3info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-10T13:08:34Zoai:ri.conicet.gov.ar:11336/134666instacron:CONICETInstitucionalhttp://ri.conicet.gov.ar/Organismo científico-tecnológicoNo correspondehttp://ri.conicet.gov.ar/oai/requestdasensio@conicet.gov.ar; lcarlino@conicet.gov.arArgentinaNo correspondeNo correspondeNo correspondeopendoar:34982025-09-10 13:08:34.647CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv A search for C-H···O type hydrogen bonds in Lamivudine (3TC). An exploratory conformational and electronic analysis
title A search for C-H···O type hydrogen bonds in Lamivudine (3TC). An exploratory conformational and electronic analysis
spellingShingle A search for C-H···O type hydrogen bonds in Lamivudine (3TC). An exploratory conformational and electronic analysis
Fidanza, N. G.
AB INITIO
ATOMS IN MOLECULES (AIM)
CONFORMATIONAL ANALYSIS
DENSITY FUNCTIONAL THEORY (DFT)
HF
HYDROGEN BOND
TOPOLOGICAL ANALYSIS OF ELECTRON DENSITY
title_short A search for C-H···O type hydrogen bonds in Lamivudine (3TC). An exploratory conformational and electronic analysis
title_full A search for C-H···O type hydrogen bonds in Lamivudine (3TC). An exploratory conformational and electronic analysis
title_fullStr A search for C-H···O type hydrogen bonds in Lamivudine (3TC). An exploratory conformational and electronic analysis
title_full_unstemmed A search for C-H···O type hydrogen bonds in Lamivudine (3TC). An exploratory conformational and electronic analysis
title_sort A search for C-H···O type hydrogen bonds in Lamivudine (3TC). An exploratory conformational and electronic analysis
dc.creator.none.fl_str_mv Fidanza, N. G.
Suvire, Fernando Daniel
Sosa, Gladis Laura
Lobayan, Rosana Maria
Enriz, Ricardo Daniel
Peruchena, Nelida Maria
author Fidanza, N. G.
author_facet Fidanza, N. G.
Suvire, Fernando Daniel
Sosa, Gladis Laura
Lobayan, Rosana Maria
Enriz, Ricardo Daniel
Peruchena, Nelida Maria
author_role author
author2 Suvire, Fernando Daniel
Sosa, Gladis Laura
Lobayan, Rosana Maria
Enriz, Ricardo Daniel
Peruchena, Nelida Maria
author2_role author
author
author
author
author
dc.subject.none.fl_str_mv AB INITIO
ATOMS IN MOLECULES (AIM)
CONFORMATIONAL ANALYSIS
DENSITY FUNCTIONAL THEORY (DFT)
HF
HYDROGEN BOND
TOPOLOGICAL ANALYSIS OF ELECTRON DENSITY
topic AB INITIO
ATOMS IN MOLECULES (AIM)
CONFORMATIONAL ANALYSIS
DENSITY FUNCTIONAL THEORY (DFT)
HF
HYDROGEN BOND
TOPOLOGICAL ANALYSIS OF ELECTRON DENSITY
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.3
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv A conformational study of the molecule Lamivudine (3TC), or cis-1-[2′-hydroxymethyl-5′-(1,3-oxathiolanyl)] cytosine, was carried out. Rotation about the C-N bond (φ1) and about the C-CH2(OH) bond (φ2), which connects the hydroxymethyl group to the five member ring, led to a conformational potential energy surface. The conformational potential energy 2D map, obtained at the HF/3-21G level of theory, had several minima. A topological analysis of the electron density was carried out on four selected ab initio minimum energy conformations, using judiciously constructed hartree-fock (RHF) wave functions. In order to see all possible hydrogen bonding, the DFT wave function was generated using a mixed basis set; a 6-311 + +G** basis was employed on atoms involved in hydrogen bonding interactions and a 3-21G basis on all other atoms. For this analysis the theory of atoms in molecules, developed by Bader, was used. The stability of the intramolecular hydrogen bonding interactions was analyzed in terms of the results obtained.
Fil: Fidanza, N. G.. Universidad Nacional del Nordeste. Facultad de Ciencias Exactas Naturales y Agrimensura. Departamento de Química; Argentina
Fil: Suvire, Fernando Daniel. Universidad Nacional de San Luis. Facultad de Química, Bioquímica y Farmacia. Departamento de Química; Argentina
Fil: Sosa, Gladis Laura. Universidad Nacional del Nordeste. Facultad de Ciencias Exactas Naturales y Agrimensura. Departamento de Química; Argentina
Fil: Lobayan, Rosana Maria. Universidad Nacional del Nordeste. Facultad de Ciencias Exactas Naturales y Agrimensura. Departamento de Química; Argentina
Fil: Enriz, Ricardo Daniel. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - San Luis. Instituto Multidisciplinario de Investigaciones Biológicas de San Luis. Universidad Nacional de San Luis. Facultad de Ciencias Físico Matemáticas y Naturales. Instituto Multidisciplinario de Investigaciones Biológicas de San Luis; Argentina
Fil: Peruchena, Nelida Maria. Universidad Nacional del Nordeste. Facultad de Ciencias Exactas Naturales y Agrimensura. Departamento de Química; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Nordeste; Argentina
description A conformational study of the molecule Lamivudine (3TC), or cis-1-[2′-hydroxymethyl-5′-(1,3-oxathiolanyl)] cytosine, was carried out. Rotation about the C-N bond (φ1) and about the C-CH2(OH) bond (φ2), which connects the hydroxymethyl group to the five member ring, led to a conformational potential energy surface. The conformational potential energy 2D map, obtained at the HF/3-21G level of theory, had several minima. A topological analysis of the electron density was carried out on four selected ab initio minimum energy conformations, using judiciously constructed hartree-fock (RHF) wave functions. In order to see all possible hydrogen bonding, the DFT wave function was generated using a mixed basis set; a 6-311 + +G** basis was employed on atoms involved in hydrogen bonding interactions and a 3-21G basis on all other atoms. For this analysis the theory of atoms in molecules, developed by Bader, was used. The stability of the intramolecular hydrogen bonding interactions was analyzed in terms of the results obtained.
publishDate 2001
dc.date.none.fl_str_mv 2001-06-22
dc.type.none.fl_str_mv info:eu-repo/semantics/article
info:eu-repo/semantics/publishedVersion
http://purl.org/coar/resource_type/c_6501
info:ar-repo/semantics/articulo
format article
status_str publishedVersion
dc.identifier.none.fl_str_mv http://hdl.handle.net/11336/134666
Fidanza, N. G.; Suvire, Fernando Daniel; Sosa, Gladis Laura; Lobayan, Rosana Maria; Enriz, Ricardo Daniel; et al.; A search for C-H···O type hydrogen bonds in Lamivudine (3TC). An exploratory conformational and electronic analysis; Elsevier Science; Journal of Molecular Structure Theochem; 543; 1-3; 22-6-2001; 185-193
0166-1280
CONICET Digital
CONICET
url http://hdl.handle.net/11336/134666
identifier_str_mv Fidanza, N. G.; Suvire, Fernando Daniel; Sosa, Gladis Laura; Lobayan, Rosana Maria; Enriz, Ricardo Daniel; et al.; A search for C-H···O type hydrogen bonds in Lamivudine (3TC). An exploratory conformational and electronic analysis; Elsevier Science; Journal of Molecular Structure Theochem; 543; 1-3; 22-6-2001; 185-193
0166-1280
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/url/https://www.sciencedirect.com/science/article/abs/pii/S0166128001003463
info:eu-repo/semantics/altIdentifier/doi/10.1016/S0166-1280(01)00346-3
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
eu_rights_str_mv openAccess
rights_invalid_str_mv https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
dc.format.none.fl_str_mv application/pdf
application/pdf
application/pdf
application/pdf
application/pdf
dc.publisher.none.fl_str_mv Elsevier Science
publisher.none.fl_str_mv Elsevier Science
dc.source.none.fl_str_mv reponame:CONICET Digital (CONICET)
instname:Consejo Nacional de Investigaciones Científicas y Técnicas
reponame_str CONICET Digital (CONICET)
collection CONICET Digital (CONICET)
instname_str Consejo Nacional de Investigaciones Científicas y Técnicas
repository.name.fl_str_mv CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicas
repository.mail.fl_str_mv dasensio@conicet.gov.ar; lcarlino@conicet.gov.ar
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score 12.993085

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