Structural study of a novel acetylide-thiourea derivative and its evaluation as a detector of benzene

Autores
Khairul, Wan M.; Daud, Adibah Izzati; Mohd Hanifaah, Noor Azura; Arshad, Suhana; Razak, Ibrahim Abdul; Zuki, Hafiza Mohamed; Erben, Mauricio Federico
Año de publicación
2017
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
The new derivative 1-hexanoyl-3-(4-p-tolylethynyl-phenyl)-thiourea (APHX) was synthesised by the addition reaction between 4[4-aminophenyl] ethynyltoluene and hexanoyl isothiocyanate in acetone. The acetylide group was incorporated by using Sonogashira cross-coupling reaction allowing for the preparation of acetylide-thiourea compound. APHX was then elucidated via single crystal X-ray crystallography analysis, spectroscopic and elemental analysis by Fourier Transform Infrared (FT-IR) spectroscopy, 1H and 13C Nuclear Magnetic Resonance (NMR), UV–visible analysis, CHNS-elemental analysis. APHX was also evaluated theoretically via density functional theory (DFT) approach. APHX was fabricated onto glass substrate via drop-cast technique prior to act as optical thin-film and its performance as volatile organic compounds (VOCs) sensor was investigated through the difference in UV–vis profile before and after exposure towards benzene. Preliminary findings revealed that APHX showed interaction towards benzene with about 48% sensitivity. According to thermogravimetric studies, APHX showed good thermal stability, without decomposition up to ca. 190 °C. Whilst, crystal structure of APHX consists in a nearly planar acylthiourea moiety with the CO and CS bonds utilizing trans position, favoring by an intramolecular NH⋯OC hydrogen bonds. The alkyl chain is oriented 90° with respect to acylthiourea group. The phenyls group in the 1-methyl-4-(phenylethynyl)benzene moieties are mutually planar and slightly twisted with respect to the acylthiourea plane. Centrosymmetric dimers generated by intermolecular NH⋯SC and CH⋯SC hydrogen bonds forming R22 (8) and R21(6) motifs are present in the crystals. The interaction between APHX with benzene has been modelled and calculated using density functional theory (DFT) via Gaussian 09 software package and the preferred sites of binding are located at the acylthiourea group.
Fil: Khairul, Wan M.. Universiti Malaysia Terengganu; Malasia
Fil: Daud, Adibah Izzati. Universiti Malaysia Terengganu; Malasia. Universiti Malaysia Perlis; Malasia
Fil: Mohd Hanifaah, Noor Azura. Universiti Malaysia Terengganu; Malasia
Fil: Arshad, Suhana. Universiti Sains Malaysia; Malasia
Fil: Razak, Ibrahim Abdul. Universiti Sains Malaysia; Malasia
Fil: Zuki, Hafiza Mohamed. Universiti Malaysia Terengganu; Malasia
Fil: Erben, Mauricio Federico. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Centro de Química Inorgánica "Dr. Pedro J. Aymonino". Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Centro de Química Inorgánica "Dr. Pedro J. Aymonino"; Argentina
Materia
Acetylide
Crystallography
Dft
Spectroscopy
Synthesis
Thiourea
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:11336/48254
Acceder
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oai_identifier_str oai:ri.conicet.gov.ar:11336/48254
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Structural study of a novel acetylide-thiourea derivative and its evaluation as a detector of benzeneKhairul, Wan M.Daud, Adibah IzzatiMohd Hanifaah, Noor AzuraArshad, SuhanaRazak, Ibrahim AbdulZuki, Hafiza MohamedErben, Mauricio FedericoAcetylideCrystallographyDftSpectroscopySynthesisThioureahttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1The new derivative 1-hexanoyl-3-(4-p-tolylethynyl-phenyl)-thiourea (APHX) was synthesised by the addition reaction between 4[4-aminophenyl] ethynyltoluene and hexanoyl isothiocyanate in acetone. The acetylide group was incorporated by using Sonogashira cross-coupling reaction allowing for the preparation of acetylide-thiourea compound. APHX was then elucidated via single crystal X-ray crystallography analysis, spectroscopic and elemental analysis by Fourier Transform Infrared (FT-IR) spectroscopy, 1H and 13C Nuclear Magnetic Resonance (NMR), UV–visible analysis, CHNS-elemental analysis. APHX was also evaluated theoretically via density functional theory (DFT) approach. APHX was fabricated onto glass substrate via drop-cast technique prior to act as optical thin-film and its performance as volatile organic compounds (VOCs) sensor was investigated through the difference in UV–vis profile before and after exposure towards benzene. Preliminary findings revealed that APHX showed interaction towards benzene with about 48% sensitivity. According to thermogravimetric studies, APHX showed good thermal stability, without decomposition up to ca. 190 °C. Whilst, crystal structure of APHX consists in a nearly planar acylthiourea moiety with the CO and CS bonds utilizing trans position, favoring by an intramolecular NH⋯OC hydrogen bonds. The alkyl chain is oriented 90° with respect to acylthiourea group. The phenyls group in the 1-methyl-4-(phenylethynyl)benzene moieties are mutually planar and slightly twisted with respect to the acylthiourea plane. Centrosymmetric dimers generated by intermolecular NH⋯SC and CH⋯SC hydrogen bonds forming R22 (8) and R21(6) motifs are present in the crystals. The interaction between APHX with benzene has been modelled and calculated using density functional theory (DFT) via Gaussian 09 software package and the preferred sites of binding are located at the acylthiourea group.Fil: Khairul, Wan M.. Universiti Malaysia Terengganu; MalasiaFil: Daud, Adibah Izzati. Universiti Malaysia Terengganu; Malasia. Universiti Malaysia Perlis; MalasiaFil: Mohd Hanifaah, Noor Azura. Universiti Malaysia Terengganu; MalasiaFil: Arshad, Suhana. Universiti Sains Malaysia; MalasiaFil: Razak, Ibrahim Abdul. Universiti Sains Malaysia; MalasiaFil: Zuki, Hafiza Mohamed. Universiti Malaysia Terengganu; MalasiaFil: Erben, Mauricio Federico. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Centro de Química Inorgánica "Dr. Pedro J. Aymonino". Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Centro de Química Inorgánica "Dr. Pedro J. Aymonino"; ArgentinaElsevier Science2017-07info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/48254Khairul, Wan M.; Daud, Adibah Izzati; Mohd Hanifaah, Noor Azura; Arshad, Suhana; Razak, Ibrahim Abdul; et al.; Structural study of a novel acetylide-thiourea derivative and its evaluation as a detector of benzene; Elsevier Science; Journal of Molecular Structure; 1139; 7-2017; 353-3610022-2860CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/doi/10.1016/j.molstruc.2017.03.065info:eu-repo/semantics/altIdentifier/url/https://www.sciencedirect.com/science/article/pii/S0022286017303538info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-29T09:52:49Zoai:ri.conicet.gov.ar:11336/48254instacron: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:34982025-09-29 09:52:49.992CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Structural study of a novel acetylide-thiourea derivative and its evaluation as a detector of benzene
title Structural study of a novel acetylide-thiourea derivative and its evaluation as a detector of benzene
spellingShingle Structural study of a novel acetylide-thiourea derivative and its evaluation as a detector of benzene
Khairul, Wan M.
Acetylide
Crystallography
Dft
Spectroscopy
Synthesis
Thiourea
title_short Structural study of a novel acetylide-thiourea derivative and its evaluation as a detector of benzene
title_full Structural study of a novel acetylide-thiourea derivative and its evaluation as a detector of benzene
title_fullStr Structural study of a novel acetylide-thiourea derivative and its evaluation as a detector of benzene
title_full_unstemmed Structural study of a novel acetylide-thiourea derivative and its evaluation as a detector of benzene
title_sort Structural study of a novel acetylide-thiourea derivative and its evaluation as a detector of benzene
dc.creator.none.fl_str_mv Khairul, Wan M.
Daud, Adibah Izzati
Mohd Hanifaah, Noor Azura
Arshad, Suhana
Razak, Ibrahim Abdul
Zuki, Hafiza Mohamed
Erben, Mauricio Federico
author Khairul, Wan M.
author_facet Khairul, Wan M.
Daud, Adibah Izzati
Mohd Hanifaah, Noor Azura
Arshad, Suhana
Razak, Ibrahim Abdul
Zuki, Hafiza Mohamed
Erben, Mauricio Federico
author_role author
author2 Daud, Adibah Izzati
Mohd Hanifaah, Noor Azura
Arshad, Suhana
Razak, Ibrahim Abdul
Zuki, Hafiza Mohamed
Erben, Mauricio Federico
author2_role author
author
author
author
author
author
dc.subject.none.fl_str_mv Acetylide
Crystallography
Dft
Spectroscopy
Synthesis
Thiourea
topic Acetylide
Crystallography
Dft
Spectroscopy
Synthesis
Thiourea
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv The new derivative 1-hexanoyl-3-(4-p-tolylethynyl-phenyl)-thiourea (APHX) was synthesised by the addition reaction between 4[4-aminophenyl] ethynyltoluene and hexanoyl isothiocyanate in acetone. The acetylide group was incorporated by using Sonogashira cross-coupling reaction allowing for the preparation of acetylide-thiourea compound. APHX was then elucidated via single crystal X-ray crystallography analysis, spectroscopic and elemental analysis by Fourier Transform Infrared (FT-IR) spectroscopy, 1H and 13C Nuclear Magnetic Resonance (NMR), UV–visible analysis, CHNS-elemental analysis. APHX was also evaluated theoretically via density functional theory (DFT) approach. APHX was fabricated onto glass substrate via drop-cast technique prior to act as optical thin-film and its performance as volatile organic compounds (VOCs) sensor was investigated through the difference in UV–vis profile before and after exposure towards benzene. Preliminary findings revealed that APHX showed interaction towards benzene with about 48% sensitivity. According to thermogravimetric studies, APHX showed good thermal stability, without decomposition up to ca. 190 °C. Whilst, crystal structure of APHX consists in a nearly planar acylthiourea moiety with the CO and CS bonds utilizing trans position, favoring by an intramolecular NH⋯OC hydrogen bonds. The alkyl chain is oriented 90° with respect to acylthiourea group. The phenyls group in the 1-methyl-4-(phenylethynyl)benzene moieties are mutually planar and slightly twisted with respect to the acylthiourea plane. Centrosymmetric dimers generated by intermolecular NH⋯SC and CH⋯SC hydrogen bonds forming R22 (8) and R21(6) motifs are present in the crystals. The interaction between APHX with benzene has been modelled and calculated using density functional theory (DFT) via Gaussian 09 software package and the preferred sites of binding are located at the acylthiourea group.
Fil: Khairul, Wan M.. Universiti Malaysia Terengganu; Malasia
Fil: Daud, Adibah Izzati. Universiti Malaysia Terengganu; Malasia. Universiti Malaysia Perlis; Malasia
Fil: Mohd Hanifaah, Noor Azura. Universiti Malaysia Terengganu; Malasia
Fil: Arshad, Suhana. Universiti Sains Malaysia; Malasia
Fil: Razak, Ibrahim Abdul. Universiti Sains Malaysia; Malasia
Fil: Zuki, Hafiza Mohamed. Universiti Malaysia Terengganu; Malasia
Fil: Erben, Mauricio Federico. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Centro de Química Inorgánica "Dr. Pedro J. Aymonino". Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Centro de Química Inorgánica "Dr. Pedro J. Aymonino"; Argentina
description The new derivative 1-hexanoyl-3-(4-p-tolylethynyl-phenyl)-thiourea (APHX) was synthesised by the addition reaction between 4[4-aminophenyl] ethynyltoluene and hexanoyl isothiocyanate in acetone. The acetylide group was incorporated by using Sonogashira cross-coupling reaction allowing for the preparation of acetylide-thiourea compound. APHX was then elucidated via single crystal X-ray crystallography analysis, spectroscopic and elemental analysis by Fourier Transform Infrared (FT-IR) spectroscopy, 1H and 13C Nuclear Magnetic Resonance (NMR), UV–visible analysis, CHNS-elemental analysis. APHX was also evaluated theoretically via density functional theory (DFT) approach. APHX was fabricated onto glass substrate via drop-cast technique prior to act as optical thin-film and its performance as volatile organic compounds (VOCs) sensor was investigated through the difference in UV–vis profile before and after exposure towards benzene. Preliminary findings revealed that APHX showed interaction towards benzene with about 48% sensitivity. According to thermogravimetric studies, APHX showed good thermal stability, without decomposition up to ca. 190 °C. Whilst, crystal structure of APHX consists in a nearly planar acylthiourea moiety with the CO and CS bonds utilizing trans position, favoring by an intramolecular NH⋯OC hydrogen bonds. The alkyl chain is oriented 90° with respect to acylthiourea group. The phenyls group in the 1-methyl-4-(phenylethynyl)benzene moieties are mutually planar and slightly twisted with respect to the acylthiourea plane. Centrosymmetric dimers generated by intermolecular NH⋯SC and CH⋯SC hydrogen bonds forming R22 (8) and R21(6) motifs are present in the crystals. The interaction between APHX with benzene has been modelled and calculated using density functional theory (DFT) via Gaussian 09 software package and the preferred sites of binding are located at the acylthiourea group.
publishDate 2017
dc.date.none.fl_str_mv 2017-07
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/11336/48254
Khairul, Wan M.; Daud, Adibah Izzati; Mohd Hanifaah, Noor Azura; Arshad, Suhana; Razak, Ibrahim Abdul; et al.; Structural study of a novel acetylide-thiourea derivative and its evaluation as a detector of benzene; Elsevier Science; Journal of Molecular Structure; 1139; 7-2017; 353-361
0022-2860
CONICET Digital
CONICET
url http://hdl.handle.net/11336/48254
identifier_str_mv Khairul, Wan M.; Daud, Adibah Izzati; Mohd Hanifaah, Noor Azura; Arshad, Suhana; Razak, Ibrahim Abdul; et al.; Structural study of a novel acetylide-thiourea derivative and its evaluation as a detector of benzene; Elsevier Science; Journal of Molecular Structure; 1139; 7-2017; 353-361
0022-2860
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/doi/10.1016/j.molstruc.2017.03.065
info:eu-repo/semantics/altIdentifier/url/https://www.sciencedirect.com/science/article/pii/S0022286017303538
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
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 13.070432

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