R. Alan Aitken, David B. Cordes, Aidan P. McKay, Dheirya K. Sonecha
The X-ray structure of the title compound has been determined for the first time. This features ribbons formed by two parallel chains of molecules joined by C=O···H–N hydrogen bonding, which are then cross-linked by C=O···H–O hydrogen bonds. The structure is compared to those of closely related compounds.
{"title":"tert-Butyl N-Hydroxycarbamate (N-Boc-Hydroxylamine)","authors":"R. Alan Aitken, David B. Cordes, Aidan P. McKay, Dheirya K. Sonecha","doi":"10.3390/m1728","DOIUrl":"https://doi.org/10.3390/m1728","url":null,"abstract":"The X-ray structure of the title compound has been determined for the first time. This features ribbons formed by two parallel chains of molecules joined by C=O···H–N hydrogen bonding, which are then cross-linked by C=O···H–O hydrogen bonds. The structure is compared to those of closely related compounds.","PeriodicalId":18761,"journal":{"name":"Molbank","volume":"220 1","pages":"0"},"PeriodicalIF":0.0,"publicationDate":"2023-09-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"135206239","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Dayi Liu, Régis Guillot, Sylvie Robin, David J. Aitken
trans-3-Benzyloxycarbonylamino-1-methyl-3-(methylcarbamoyl)azetidine-1-oxide was prepared by stereoselective oxidation of the corresponding azetidine precursor. The stable molecule was characterized in a low-polarity solution by IR, 1H-NMR and 13C-NMR, and in the solid state as a co-crystal with water by X-Ray diffraction. The N-oxide function made a strong intramolecular 7-membered ring hydrogen bond with the methyl amide NH in solution and formed an intermolecular H-bond with the carbamate NH in a neighboring molecule in the solid state.
{"title":"trans-3-Benzyloxycarbonylamino-1-methyl-3-(methylcarbamoyl)azetidine-1-oxide","authors":"Dayi Liu, Régis Guillot, Sylvie Robin, David J. Aitken","doi":"10.3390/m1726","DOIUrl":"https://doi.org/10.3390/m1726","url":null,"abstract":"trans-3-Benzyloxycarbonylamino-1-methyl-3-(methylcarbamoyl)azetidine-1-oxide was prepared by stereoselective oxidation of the corresponding azetidine precursor. The stable molecule was characterized in a low-polarity solution by IR, 1H-NMR and 13C-NMR, and in the solid state as a co-crystal with water by X-Ray diffraction. The N-oxide function made a strong intramolecular 7-membered ring hydrogen bond with the methyl amide NH in solution and formed an intermolecular H-bond with the carbamate NH in a neighboring molecule in the solid state.","PeriodicalId":18761,"journal":{"name":"Molbank","volume":"24 1","pages":"0"},"PeriodicalIF":0.0,"publicationDate":"2023-09-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"135439641","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Panagiotis Kouvatsis, Dimitrios Glykos, John C. Plakatouras, Gerasimos Malandrinos
A new heteroleptic Cu(I) complex, [Cu(L)(PPh3)2][BF4] (L = 6-(furan-2-yl)-2,2′-bipyridine; PPh3 = triphenylphosphine), was successfully synthesized and characterized. Its molecular structure was determined using X-ray crystallography, and NMR as well as HR-ESI-MS data confirm the compound’s integrity in solution. The complex exhibits emission solely in the solid state (λem = 576 nm) and demonstrates a photoluminescence quantum yield of 2.5%.
{"title":"[6-(Furan-2-yl)-2,2′-bipyridine]bis(triphenylphosphine) Copper(I) Tetrafluoroborate","authors":"Panagiotis Kouvatsis, Dimitrios Glykos, John C. Plakatouras, Gerasimos Malandrinos","doi":"10.3390/m1724","DOIUrl":"https://doi.org/10.3390/m1724","url":null,"abstract":"A new heteroleptic Cu(I) complex, [Cu(L)(PPh3)2][BF4] (L = 6-(furan-2-yl)-2,2′-bipyridine; PPh3 = triphenylphosphine), was successfully synthesized and characterized. Its molecular structure was determined using X-ray crystallography, and NMR as well as HR-ESI-MS data confirm the compound’s integrity in solution. The complex exhibits emission solely in the solid state (λem = 576 nm) and demonstrates a photoluminescence quantum yield of 2.5%.","PeriodicalId":18761,"journal":{"name":"Molbank","volume":"18 1","pages":"0"},"PeriodicalIF":0.0,"publicationDate":"2023-09-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"135781960","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
[Sn(OSO3)2(TPyHP)](HSO4)2∙8H2O (1), an ionic Sn(IV)-porphyrin complex, was prepared by reacting [Sn(OH2)2TPyP] with dilute sulfuric acid. X-ray structural analysis revealed that the zwitterionic [Sn(OSO3)2TPyHP]2+ species consists of two anionic axial Sn–O–SO3 units and four peripheral pyridinium moieties, with an overall dicationic charge balanced by two hydrogen sulfate (HSO4−) counter-anions. Ionic hydrogen bonding between the oxygen atoms of axial sulfato ligands and the peripheral pyridinium groups of adjacent Sn(IV)-porphyrin cations led to the formation of a 1D channel filled with counter-anions and water molecules. The supramolecular self-assembly of 1 was further characterized using various spectroscopic techniques, including 1H NMR spectroscopy, elemental analysis, ESI-mass spectrometry, UV-vis spectroscopy, fluorescence spectroscopy, FT-IR spectroscopy, thermogravimetric analysis (TGA), and powder X-ray diffractometry. The zwitterionic [Sn(OSO3)2TPyHP]2+ complex is a structurally well-defined complementary scaffold involved in supramolecular self-assembly. This novel class of ion-assembled metalloporphyrin is a potential functional porphyrin material used in ion exchange applications.
[Sn(OSO3)2(TPyHP)](HSO4)2∙8H2O(1)是一种离子型Sn(IV)-卟啉络合物，由[Sn(OH2)2TPyP]与稀硫酸反应而得。x射线结构分析表明，两性离子[Sn(OSO3)2TPyHP]2+由两个阴离子的轴向Sn - o - so3单元和四个外围的吡啶基团组成，总体上由两个硫酸氢(HSO4−)反阴离子平衡。轴向磺胺配体的氧原子与相邻Sn(IV)-卟啉阳离子的外围吡啶基团之间的离子氢键导致形成充满反阴离子和水分子的一维通道。利用各种光谱技术，包括1H NMR光谱、元素分析、esi -质谱、UV-vis光谱、荧光光谱、FT-IR光谱、热重分析(TGA)和粉末x射线衍射，进一步表征了1的超分子自组装。两性离子[Sn(OSO3)2TPyHP]2+配合物是一种结构明确的互补支架，参与超分子自组装。这种新型的离子组装金属卟啉是一种潜在的用于离子交换应用的功能卟啉材料。
{"title":"Supramolecular Self-Assembly of the Zwitterionic Sn(IV)-Porphyrin Complex","authors":"Nirmal Kumar Shee, Hee-Joon Kim","doi":"10.3390/m1723","DOIUrl":"https://doi.org/10.3390/m1723","url":null,"abstract":"[Sn(OSO3)2(TPyHP)](HSO4)2∙8H2O (1), an ionic Sn(IV)-porphyrin complex, was prepared by reacting [Sn(OH2)2TPyP] with dilute sulfuric acid. X-ray structural analysis revealed that the zwitterionic [Sn(OSO3)2TPyHP]2+ species consists of two anionic axial Sn–O–SO3 units and four peripheral pyridinium moieties, with an overall dicationic charge balanced by two hydrogen sulfate (HSO4−) counter-anions. Ionic hydrogen bonding between the oxygen atoms of axial sulfato ligands and the peripheral pyridinium groups of adjacent Sn(IV)-porphyrin cations led to the formation of a 1D channel filled with counter-anions and water molecules. The supramolecular self-assembly of 1 was further characterized using various spectroscopic techniques, including 1H NMR spectroscopy, elemental analysis, ESI-mass spectrometry, UV-vis spectroscopy, fluorescence spectroscopy, FT-IR spectroscopy, thermogravimetric analysis (TGA), and powder X-ray diffractometry. The zwitterionic [Sn(OSO3)2TPyHP]2+ complex is a structurally well-defined complementary scaffold involved in supramolecular self-assembly. This novel class of ion-assembled metalloporphyrin is a potential functional porphyrin material used in ion exchange applications.","PeriodicalId":18761,"journal":{"name":"Molbank","volume":"11 1","pages":"0"},"PeriodicalIF":0.0,"publicationDate":"2023-09-12","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"135830101","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Thomas Gelbrich, Jascha Schinke, Ulrich J. Griesser
The two-component compound formed by codeine and cyclopentobarbital was produced using grinding techniques and through evaporation from alcoholic solutions. The cocrystal nature of this phase was established unequivocally through single crystal X-ray structure determination. The asymmetric unit contains one formula unit. In the cyclopentobarbital molecule, the cyclopentenyl ring is disordered over two positions related by a rotation of approximately 180° about its C—C bond to the pyrimidine ring. The two NH groups of the cyclopentobarbital molecule form N—H⋯N and N—H⋯O bonds to piperidine and hydroxyl groups, respectively, belonging to different codeine molecules. In addition, the hydroxyl and methoxy groups of neighboring codeine molecules are linked by O—H⋯O interactions, resulting in a H-bonded framework structure of codeine and cyclopentobarbital molecules. The cocrystal was also characterized using thermal analysis, X-ray powder diffraction and IR spectroscopy.
{"title":"Cocrystal of Codeine and Cyclopentobarbital","authors":"Thomas Gelbrich, Jascha Schinke, Ulrich J. Griesser","doi":"10.3390/m1722","DOIUrl":"https://doi.org/10.3390/m1722","url":null,"abstract":"The two-component compound formed by codeine and cyclopentobarbital was produced using grinding techniques and through evaporation from alcoholic solutions. The cocrystal nature of this phase was established unequivocally through single crystal X-ray structure determination. The asymmetric unit contains one formula unit. In the cyclopentobarbital molecule, the cyclopentenyl ring is disordered over two positions related by a rotation of approximately 180° about its C—C bond to the pyrimidine ring. The two NH groups of the cyclopentobarbital molecule form N—H⋯N and N—H⋯O bonds to piperidine and hydroxyl groups, respectively, belonging to different codeine molecules. In addition, the hydroxyl and methoxy groups of neighboring codeine molecules are linked by O—H⋯O interactions, resulting in a H-bonded framework structure of codeine and cyclopentobarbital molecules. The cocrystal was also characterized using thermal analysis, X-ray powder diffraction and IR spectroscopy.","PeriodicalId":18761,"journal":{"name":"Molbank","volume":"43 1","pages":"0"},"PeriodicalIF":0.0,"publicationDate":"2023-09-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"135980032","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Y. E. Ryzhkova, Varvara M. Kalashnikova, F. V. Ryzhkov, A. N. Fakhrutdinov, M. Elinson
Pseudo-multicomponent reactions (Pseudo-MCRs) have led to a variety of compounds with interesting biological properties, especially desirable in the pharmaceutical industry. The isatin nucleus could be considered a privileged scaffold for the design of biologically active substances. Dimedone is an interesting and versatile molecule for most organic transformations, especially one-pot and multicomponent reactions. Xanthene derivatives are still an attractive research field for both academia investigations and industry. In this investigation, a simple and efficient tandem Knoevenagel–Michael protocol with subsequent cyclization for the synthesis of the previously unknown 4a’-hydroxy-3′,3′,5,6′,6′,7-hexamethyl-3′,4′,4a’,6′,7′,9a′-hexahydrospiro[indole-3,9′-xanthene]-1′,2,8′(1H,2′H,5′H)-trione was elaborated. The suggested method is based on the pseudo-MCR of 5,7-dimethylisatin and dimedone. The structure of the earlier unknown compound was proven using 1H, 13C-NMR, and IR spectroscopy, mass spectrometry, and elemental analysis. To compare the developed protocol with the existing ones, unsubstituted spiro[indole-3,9′-xanthene] was synthesized. Its structure has been proven using two-dimensional (2D) NMR spectroscopy techniques.
{"title":"4a’-Hydroxy-3′,3′,5,6′,6′,7-hexamethyl-3′,4′,4a’,6′,7′,9a′-hexahydrospiro[indole-3,9′-xanthene]-1′,2,8′(1H,2′H,5′H)-trione","authors":"Y. E. Ryzhkova, Varvara M. Kalashnikova, F. V. Ryzhkov, A. N. Fakhrutdinov, M. Elinson","doi":"10.3390/m1721","DOIUrl":"https://doi.org/10.3390/m1721","url":null,"abstract":"Pseudo-multicomponent reactions (Pseudo-MCRs) have led to a variety of compounds with interesting biological properties, especially desirable in the pharmaceutical industry. The isatin nucleus could be considered a privileged scaffold for the design of biologically active substances. Dimedone is an interesting and versatile molecule for most organic transformations, especially one-pot and multicomponent reactions. Xanthene derivatives are still an attractive research field for both academia investigations and industry. In this investigation, a simple and efficient tandem Knoevenagel–Michael protocol with subsequent cyclization for the synthesis of the previously unknown 4a’-hydroxy-3′,3′,5,6′,6′,7-hexamethyl-3′,4′,4a’,6′,7′,9a′-hexahydrospiro[indole-3,9′-xanthene]-1′,2,8′(1H,2′H,5′H)-trione was elaborated. The suggested method is based on the pseudo-MCR of 5,7-dimethylisatin and dimedone. The structure of the earlier unknown compound was proven using 1H, 13C-NMR, and IR spectroscopy, mass spectrometry, and elemental analysis. To compare the developed protocol with the existing ones, unsubstituted spiro[indole-3,9′-xanthene] was synthesized. Its structure has been proven using two-dimensional (2D) NMR spectroscopy techniques.","PeriodicalId":18761,"journal":{"name":"Molbank","volume":" ","pages":""},"PeriodicalIF":0.6,"publicationDate":"2023-09-08","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"49347865","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Bakr F. Abdel-Wahab, A. Mabied, James C. Fettinger, A. Farahat
The reaction of 2-bromo-1-(5-methyl-1-(4-nitrophenyl)-1H-1,2,3-triazol-4-yl)ethan-1-one (1) with 4-amino-5-((2,4-dichlorophenoxy)methyl)-4H-1,2,4-triazole-3-thiol (2) in absolute ethanol in the presence of triethyl amine as catalyst gave 2-((4-amino-5-((2,4-dichlorophenoxy)methyl)-4H-1,2,4-triazol-3-yl)thio)-1-(5-methyl-1-(4-nitrophenyl)-1H-1,2,3-triazol-4-yl)ethan-1-one (3) in 73% yield. The structure of the title heterocycle (3) was confirmed by X-ray single crystal diffraction and spectral analyses (NMR and IR).
{"title":"2-((4-Amino-5-((2,4-dichlorophenoxy)methyl)-4H-1,2,4-triazol-3-yl)thio)-1-(5-methyl-1-(4-nitrophenyl)-1H-1,2,3-triazol-4-yl)ethan-1-one","authors":"Bakr F. Abdel-Wahab, A. Mabied, James C. Fettinger, A. Farahat","doi":"10.3390/m1720","DOIUrl":"https://doi.org/10.3390/m1720","url":null,"abstract":"The reaction of 2-bromo-1-(5-methyl-1-(4-nitrophenyl)-1H-1,2,3-triazol-4-yl)ethan-1-one (1) with 4-amino-5-((2,4-dichlorophenoxy)methyl)-4H-1,2,4-triazole-3-thiol (2) in absolute ethanol in the presence of triethyl amine as catalyst gave 2-((4-amino-5-((2,4-dichlorophenoxy)methyl)-4H-1,2,4-triazol-3-yl)thio)-1-(5-methyl-1-(4-nitrophenyl)-1H-1,2,3-triazol-4-yl)ethan-1-one (3) in 73% yield. The structure of the title heterocycle (3) was confirmed by X-ray single crystal diffraction and spectral analyses (NMR and IR).","PeriodicalId":18761,"journal":{"name":"Molbank","volume":" ","pages":""},"PeriodicalIF":0.6,"publicationDate":"2023-09-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"48898290","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Mohamed Kdider, C. Elléouet, F. Pétillon, P. Schollhammer
The di-iron carbonyl dithiolene bridged complex [Fe2(CO)6(µ-S2C2(CO2Me)2)] (1) reacts with 1 equivalent of phosphane PR3 (R = Ph, OMe) to give, as major products, monosubstituted derivatives [Fe2(CO)5L(µ-S2C2(CO2Me)2)] (L = PPh3 (2), P(OMe)3 (3)). In the presence of an excess (3–4 equiv.) of P(OMe)3, the cleavage of 1 arises partly and a mixture of the mononuclear species [Fe(CO)(P(OMe)3)2(κ2-S2C2(CO2Me)2)] (4) and 3 is obtained. The compounds 2–4 were analyzed by IR and 1H, 31P-{1H} NMR spectroscopies. Their structures in solid state were determined by X-ray diffraction analyses, which accord with their spectroscopic characteristics.
{"title":"Mono- and Dinuclear Carbonyl Dithiolene Complexes Related to the [FeFe]-Hydrogenases","authors":"Mohamed Kdider, C. Elléouet, F. Pétillon, P. Schollhammer","doi":"10.3390/m1719","DOIUrl":"https://doi.org/10.3390/m1719","url":null,"abstract":"The di-iron carbonyl dithiolene bridged complex [Fe2(CO)6(µ-S2C2(CO2Me)2)] (1) reacts with 1 equivalent of phosphane PR3 (R = Ph, OMe) to give, as major products, monosubstituted derivatives [Fe2(CO)5L(µ-S2C2(CO2Me)2)] (L = PPh3 (2), P(OMe)3 (3)). In the presence of an excess (3–4 equiv.) of P(OMe)3, the cleavage of 1 arises partly and a mixture of the mononuclear species [Fe(CO)(P(OMe)3)2(κ2-S2C2(CO2Me)2)] (4) and 3 is obtained. The compounds 2–4 were analyzed by IR and 1H, 31P-{1H} NMR spectroscopies. Their structures in solid state were determined by X-ray diffraction analyses, which accord with their spectroscopic characteristics.","PeriodicalId":18761,"journal":{"name":"Molbank","volume":" ","pages":""},"PeriodicalIF":0.6,"publicationDate":"2023-09-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"48150251","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Luka Ciber, Helena Brodnik, F. Požgan, J. Svete, B. Štefane, Uroš Grošelj
A monosubstituted benzene-1,2-diamine building block, N1-(3,5-bis(trifluoromethyl)benzyl)benzene-1,2-diamine, was prepared in two steps from commercially available 3,5-bis(trifluoromethyl)benzylamine and 1-fluoro-2-nitrobenzene, while the use of 3,5-bis(trifluoromethyl)aniline as the starting amine gave a triarylamine, N,N-bis(2-nitrophenyl)-3,5-bis(trifluoromethyl)aniline. The structures of the newly synthesized compounds were fully characterized.
{"title":"Synthesis of N1-(3,5-Bis(trifluoromethyl)benzyl)benzene-1,2-diamine and N,N-Bis(2-nitrophenyl)-3,5-bis(trifluoromethyl)aniline","authors":"Luka Ciber, Helena Brodnik, F. Požgan, J. Svete, B. Štefane, Uroš Grošelj","doi":"10.3390/m1718","DOIUrl":"https://doi.org/10.3390/m1718","url":null,"abstract":"A monosubstituted benzene-1,2-diamine building block, N1-(3,5-bis(trifluoromethyl)benzyl)benzene-1,2-diamine, was prepared in two steps from commercially available 3,5-bis(trifluoromethyl)benzylamine and 1-fluoro-2-nitrobenzene, while the use of 3,5-bis(trifluoromethyl)aniline as the starting amine gave a triarylamine, N,N-bis(2-nitrophenyl)-3,5-bis(trifluoromethyl)aniline. The structures of the newly synthesized compounds were fully characterized.","PeriodicalId":18761,"journal":{"name":"Molbank","volume":" ","pages":""},"PeriodicalIF":0.6,"publicationDate":"2023-09-04","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"49498859","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
The title compound N-(2,3-difluorophenyl)-2-fluorobenzamide or (Fo23) was obtained at high yield (88%) from the condensation reaction of 2-fluorobenzoyl chloride with 2,3-difluoroaniline using standard synthetic procedures. The crystal structure of Fo23 was determined at 294 (1) K using single crystal X-ray diffraction methods and represents the first regular tri-fluorinated benzamide with formula C13H8F3NO compared to the difluorinated and tetra-fluorinated analogues. In the structure, both aromatic rings are effectively co-planar, with an interplanar angle of 0.5(2)°; however, the central amide group plane is oriented by 23.17(18)° and 23.44(17)° from the aromatic rings as influenced by 1D amide⋯amide hydrogen bonds along the a-axis direction. Longer C-H⋯F/O interactions and the arrangement of a R22(12) synthon involving two C-F, a N-H and two C-H, together with C-F⋯C ring⋯ring stacking contacts, complete the interactions in the Fo23 crystal structure.
{"title":"N-(2,3-Difluorophenyl)-2-fluorobenzamide","authors":"Niall Hehir, John F. Gallagher","doi":"10.3390/m1717","DOIUrl":"https://doi.org/10.3390/m1717","url":null,"abstract":"The title compound N-(2,3-difluorophenyl)-2-fluorobenzamide or (Fo23) was obtained at high yield (88%) from the condensation reaction of 2-fluorobenzoyl chloride with 2,3-difluoroaniline using standard synthetic procedures. The crystal structure of Fo23 was determined at 294 (1) K using single crystal X-ray diffraction methods and represents the first regular tri-fluorinated benzamide with formula C13H8F3NO compared to the difluorinated and tetra-fluorinated analogues. In the structure, both aromatic rings are effectively co-planar, with an interplanar angle of 0.5(2)°; however, the central amide group plane is oriented by 23.17(18)° and 23.44(17)° from the aromatic rings as influenced by 1D amide⋯amide hydrogen bonds along the a-axis direction. Longer C-H⋯F/O interactions and the arrangement of a R22(12) synthon involving two C-F, a N-H and two C-H, together with C-F⋯C ring⋯ring stacking contacts, complete the interactions in the Fo23 crystal structure.","PeriodicalId":18761,"journal":{"name":"Molbank","volume":" ","pages":""},"PeriodicalIF":0.6,"publicationDate":"2023-09-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"45356772","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
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