X-ray, DFT, FTIR and thermal study of the antimicrobial N-benzenesulfonyl-1H-1,2,3-benzotriazole
- Autores
- Komrovsky, Fabián; Sperandeo, Norma Rebeca; Vera, Domingo Mariano Adolfo; Caira, Mino R.; Mazzieri, Maria Rosa
- Año de publicación
- 2018
- Idioma
- inglés
- Tipo de recurso
- artículo
- Estado
- versión publicada
- Descripción
- N-benzenesulfonyl-1H-1,2,3-benzotriazole (NBSBZT) is a compound with significant trypanocidal and bactericidal activities, which we reported previously. In this work a combined experimental and theoretical study of its structural and molecular properties is communicated. The crystal structure of NBSBZT was determined by single crystal X-ray diffraction. The molecular vibrations and behavior on heating of NBSBZT were investigated by Fourier Transform Infrared (FTIR) Spectroscopy, Differential Scanning Calorimetry (DSC), Thermogravimetry (TG) and Hot Stage Microscopy (HSM). In parallel, Quantum Chemical calculations based on Density Functional Theory (DFT) and Scaled Quantum Mechanics methods were used to determine the geometrical, energetic and vibrational characteristics of NBSBZT. The study demonstrated that NBSBZT crystallized in the triclinic space group P‾1 (No. 2) with two inversion-related molecules in the unit cell (Z = 2). Its overall molecular conformation can be described by two torsion angles, namely φ1 (N2–N1–S10–C13) = −94.5(2)° and φ2 (N1–S10–C13–C14) = 84.2(2)°. The minimum energy structures found by theoretical calculations showed φ1 = −67.6° and φ2 = 88.0° in vacuum; however, in water, the torsion angles were −77.5° and 88.7° respectively. The differences in φ1 (Δφ1 solid state-vacuum = 26.9° and Δφ1 solid state-water = 17.0°) could be attributed to the high intermolecular cohesive forces present in the crystal of NBSBZT. A good correlation between the experimental and theoretical mid-FTIR spectra was found. The DSC, TG and HSM results indicated that NBSBZT was a solvent-free solid, which melted at 128.8 °C but decomposed above 130 °C.
Fil: Komrovsky, Fabián. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Departamento de Farmacia; Argentina
Fil: Sperandeo, Norma Rebeca. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Departamento de Farmacia; Argentina
Fil: Vera, Domingo Mariano Adolfo. Universidad Nacional de Mar del Plata. Facultad de Ciencias Exactas y Naturales. Departamento de Química; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Mar del Plata. Instituto de Investigaciones en Biodiversidad y Biotecnología; Argentina
Fil: Caira, Mino R.. University of Cape Town; Sudáfrica
Fil: Mazzieri, Maria Rosa. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Departamento de Farmacia; Argentina - Materia
-
3D STRUCTURE
FTIR
N-BENZENESULFONYL BENZOTRIAZOLE
THERMAL ANALYSIS
TRYPANOSOMA CRUZI - Nivel de accesibilidad
- acceso abierto
- Condiciones de uso
- https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
- Repositorio
.jpg)
- Institución
- Consejo Nacional de Investigaciones Científicas y Técnicas
- OAI Identificador
- oai:ri.conicet.gov.ar:11336/100765
Ver los metadatos del registro completo
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X-ray, DFT, FTIR and thermal study of the antimicrobial N-benzenesulfonyl-1H-1,2,3-benzotriazoleKomrovsky, FabiánSperandeo, Norma RebecaVera, Domingo Mariano AdolfoCaira, Mino R.Mazzieri, Maria Rosa3D STRUCTUREFTIRN-BENZENESULFONYL BENZOTRIAZOLETHERMAL ANALYSISTRYPANOSOMA CRUZIhttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1N-benzenesulfonyl-1H-1,2,3-benzotriazole (NBSBZT) is a compound with significant trypanocidal and bactericidal activities, which we reported previously. In this work a combined experimental and theoretical study of its structural and molecular properties is communicated. The crystal structure of NBSBZT was determined by single crystal X-ray diffraction. The molecular vibrations and behavior on heating of NBSBZT were investigated by Fourier Transform Infrared (FTIR) Spectroscopy, Differential Scanning Calorimetry (DSC), Thermogravimetry (TG) and Hot Stage Microscopy (HSM). In parallel, Quantum Chemical calculations based on Density Functional Theory (DFT) and Scaled Quantum Mechanics methods were used to determine the geometrical, energetic and vibrational characteristics of NBSBZT. The study demonstrated that NBSBZT crystallized in the triclinic space group P‾1 (No. 2) with two inversion-related molecules in the unit cell (Z = 2). Its overall molecular conformation can be described by two torsion angles, namely φ1 (N2–N1–S10–C13) = −94.5(2)° and φ2 (N1–S10–C13–C14) = 84.2(2)°. The minimum energy structures found by theoretical calculations showed φ1 = −67.6° and φ2 = 88.0° in vacuum; however, in water, the torsion angles were −77.5° and 88.7° respectively. The differences in φ1 (Δφ1 solid state-vacuum = 26.9° and Δφ1 solid state-water = 17.0°) could be attributed to the high intermolecular cohesive forces present in the crystal of NBSBZT. A good correlation between the experimental and theoretical mid-FTIR spectra was found. The DSC, TG and HSM results indicated that NBSBZT was a solvent-free solid, which melted at 128.8 °C but decomposed above 130 °C.Fil: Komrovsky, Fabián. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Departamento de Farmacia; ArgentinaFil: Sperandeo, Norma Rebeca. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Departamento de Farmacia; ArgentinaFil: Vera, Domingo Mariano Adolfo. Universidad Nacional de Mar del Plata. Facultad de Ciencias Exactas y Naturales. Departamento de Química; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Mar del Plata. Instituto de Investigaciones en Biodiversidad y Biotecnología; ArgentinaFil: Caira, Mino R.. University of Cape Town; SudáfricaFil: Mazzieri, Maria Rosa. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Departamento de Farmacia; ArgentinaElsevier Science2018-03info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/100765Komrovsky, Fabián; Sperandeo, Norma Rebeca; Vera, Domingo Mariano Adolfo; Caira, Mino R.; Mazzieri, Maria Rosa; X-ray, DFT, FTIR and thermal study of the antimicrobial N-benzenesulfonyl-1H-1,2,3-benzotriazole; Elsevier Science; Journal of Molecular Structure; 1164; 3-2018; 200-2080022-2860CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/url/http://linkinghub.elsevier.com/retrieve/pii/S0022286018302953info:eu-repo/semantics/altIdentifier/doi/10.1016/j.molstruc.2018.03.012info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-29T09:38:22Zoai:ri.conicet.gov.ar:11336/100765instacron: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 09:38:22.312CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse |
| dc.title.none.fl_str_mv |
X-ray, DFT, FTIR and thermal study of the antimicrobial N-benzenesulfonyl-1H-1,2,3-benzotriazole |
| title |
X-ray, DFT, FTIR and thermal study of the antimicrobial N-benzenesulfonyl-1H-1,2,3-benzotriazole |
| spellingShingle |
X-ray, DFT, FTIR and thermal study of the antimicrobial N-benzenesulfonyl-1H-1,2,3-benzotriazole Komrovsky, Fabián 3D STRUCTURE FTIR N-BENZENESULFONYL BENZOTRIAZOLE THERMAL ANALYSIS TRYPANOSOMA CRUZI |
| title_short |
X-ray, DFT, FTIR and thermal study of the antimicrobial N-benzenesulfonyl-1H-1,2,3-benzotriazole |
| title_full |
X-ray, DFT, FTIR and thermal study of the antimicrobial N-benzenesulfonyl-1H-1,2,3-benzotriazole |
| title_fullStr |
X-ray, DFT, FTIR and thermal study of the antimicrobial N-benzenesulfonyl-1H-1,2,3-benzotriazole |
| title_full_unstemmed |
X-ray, DFT, FTIR and thermal study of the antimicrobial N-benzenesulfonyl-1H-1,2,3-benzotriazole |
| title_sort |
X-ray, DFT, FTIR and thermal study of the antimicrobial N-benzenesulfonyl-1H-1,2,3-benzotriazole |
| dc.creator.none.fl_str_mv |
Komrovsky, Fabián Sperandeo, Norma Rebeca Vera, Domingo Mariano Adolfo Caira, Mino R. Mazzieri, Maria Rosa |
| author |
Komrovsky, Fabián |
| author_facet |
Komrovsky, Fabián Sperandeo, Norma Rebeca Vera, Domingo Mariano Adolfo Caira, Mino R. Mazzieri, Maria Rosa |
| author_role |
author |
| author2 |
Sperandeo, Norma Rebeca Vera, Domingo Mariano Adolfo Caira, Mino R. Mazzieri, Maria Rosa |
| author2_role |
author author author author |
| dc.subject.none.fl_str_mv |
3D STRUCTURE FTIR N-BENZENESULFONYL BENZOTRIAZOLE THERMAL ANALYSIS TRYPANOSOMA CRUZI |
| topic |
3D STRUCTURE FTIR N-BENZENESULFONYL BENZOTRIAZOLE THERMAL ANALYSIS TRYPANOSOMA CRUZI |
| purl_subject.fl_str_mv |
https://purl.org/becyt/ford/1.4 https://purl.org/becyt/ford/1 |
| dc.description.none.fl_txt_mv |
N-benzenesulfonyl-1H-1,2,3-benzotriazole (NBSBZT) is a compound with significant trypanocidal and bactericidal activities, which we reported previously. In this work a combined experimental and theoretical study of its structural and molecular properties is communicated. The crystal structure of NBSBZT was determined by single crystal X-ray diffraction. The molecular vibrations and behavior on heating of NBSBZT were investigated by Fourier Transform Infrared (FTIR) Spectroscopy, Differential Scanning Calorimetry (DSC), Thermogravimetry (TG) and Hot Stage Microscopy (HSM). In parallel, Quantum Chemical calculations based on Density Functional Theory (DFT) and Scaled Quantum Mechanics methods were used to determine the geometrical, energetic and vibrational characteristics of NBSBZT. The study demonstrated that NBSBZT crystallized in the triclinic space group P‾1 (No. 2) with two inversion-related molecules in the unit cell (Z = 2). Its overall molecular conformation can be described by two torsion angles, namely φ1 (N2–N1–S10–C13) = −94.5(2)° and φ2 (N1–S10–C13–C14) = 84.2(2)°. The minimum energy structures found by theoretical calculations showed φ1 = −67.6° and φ2 = 88.0° in vacuum; however, in water, the torsion angles were −77.5° and 88.7° respectively. The differences in φ1 (Δφ1 solid state-vacuum = 26.9° and Δφ1 solid state-water = 17.0°) could be attributed to the high intermolecular cohesive forces present in the crystal of NBSBZT. A good correlation between the experimental and theoretical mid-FTIR spectra was found. The DSC, TG and HSM results indicated that NBSBZT was a solvent-free solid, which melted at 128.8 °C but decomposed above 130 °C. Fil: Komrovsky, Fabián. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Departamento de Farmacia; Argentina Fil: Sperandeo, Norma Rebeca. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Departamento de Farmacia; Argentina Fil: Vera, Domingo Mariano Adolfo. Universidad Nacional de Mar del Plata. Facultad de Ciencias Exactas y Naturales. Departamento de Química; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Mar del Plata. Instituto de Investigaciones en Biodiversidad y Biotecnología; Argentina Fil: Caira, Mino R.. University of Cape Town; Sudáfrica Fil: Mazzieri, Maria Rosa. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Departamento de Farmacia; Argentina |
| description |
N-benzenesulfonyl-1H-1,2,3-benzotriazole (NBSBZT) is a compound with significant trypanocidal and bactericidal activities, which we reported previously. In this work a combined experimental and theoretical study of its structural and molecular properties is communicated. The crystal structure of NBSBZT was determined by single crystal X-ray diffraction. The molecular vibrations and behavior on heating of NBSBZT were investigated by Fourier Transform Infrared (FTIR) Spectroscopy, Differential Scanning Calorimetry (DSC), Thermogravimetry (TG) and Hot Stage Microscopy (HSM). In parallel, Quantum Chemical calculations based on Density Functional Theory (DFT) and Scaled Quantum Mechanics methods were used to determine the geometrical, energetic and vibrational characteristics of NBSBZT. The study demonstrated that NBSBZT crystallized in the triclinic space group P‾1 (No. 2) with two inversion-related molecules in the unit cell (Z = 2). Its overall molecular conformation can be described by two torsion angles, namely φ1 (N2–N1–S10–C13) = −94.5(2)° and φ2 (N1–S10–C13–C14) = 84.2(2)°. The minimum energy structures found by theoretical calculations showed φ1 = −67.6° and φ2 = 88.0° in vacuum; however, in water, the torsion angles were −77.5° and 88.7° respectively. The differences in φ1 (Δφ1 solid state-vacuum = 26.9° and Δφ1 solid state-water = 17.0°) could be attributed to the high intermolecular cohesive forces present in the crystal of NBSBZT. A good correlation between the experimental and theoretical mid-FTIR spectra was found. The DSC, TG and HSM results indicated that NBSBZT was a solvent-free solid, which melted at 128.8 °C but decomposed above 130 °C. |
| publishDate |
2018 |
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2018-03 |
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http://hdl.handle.net/11336/100765 Komrovsky, Fabián; Sperandeo, Norma Rebeca; Vera, Domingo Mariano Adolfo; Caira, Mino R.; Mazzieri, Maria Rosa; X-ray, DFT, FTIR and thermal study of the antimicrobial N-benzenesulfonyl-1H-1,2,3-benzotriazole; Elsevier Science; Journal of Molecular Structure; 1164; 3-2018; 200-208 0022-2860 CONICET Digital CONICET |
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http://hdl.handle.net/11336/100765 |
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Komrovsky, Fabián; Sperandeo, Norma Rebeca; Vera, Domingo Mariano Adolfo; Caira, Mino R.; Mazzieri, Maria Rosa; X-ray, DFT, FTIR and thermal study of the antimicrobial N-benzenesulfonyl-1H-1,2,3-benzotriazole; Elsevier Science; Journal of Molecular Structure; 1164; 3-2018; 200-208 0022-2860 CONICET Digital CONICET |
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eng |
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