FRINK Linked Data Fragments server

Matches in SemOpenAlex for { <https://semopenalex.org/work/W3191410802> ?p ?o ?g. }

• W3191410802 endingPage "131271" @default.
• W3191410802 startingPage "131271" @default.
• W3191410802 abstract "• X-ray crystal structure was determined for a simple 1-acyl-urea species. • Strong intramolecular N–H•••O=C hydrogen bond is present in the crystal. • Planar pseudo six-membered ring occurs in the central 1-acyl urea group. • 1,6-Remote lpO → σ*(N–H) hyperconjugative interaction is found. • Amide bonds form R 2 2 (8) dimer motifs. Reaction of freshly prepared pivaloyl isothiocyanate with 2,3-dichloroaniline afforded the 1-(2,3-dichlorophenyl)-3-pivaloylthiourea intermediate ( 2 ) which was efficiently converted into the title urea ( 3 ) by grinding with wet silica supported potassium permanganate under solvent-free conditions in an excellent yield and purity. The structure was confirmed by the spectroscopic, elemental analysis and single crystal X-ray diffraction data. In the most stable conformation, the two C=O groups adopt a mutually opposite orientation. Intramolecular N–H•••O=C hydrogen bond occurs between the carbonyl (C=O) and urea (–NH) groups forming a six membered pseudo-ring that stabilize the most stable form. The bonding nature of this interaction has been scrutinized by using Natural Bond Orbital (NBO) population analysis, demonstrating the occurrence of a strong hyperconjugative remote interaction between the donor lone pairs located on the carbonyl oxygen and the N–H group. To visualize the intermolecular interactions in the crystal of the title compound, a Hirshfeld surface (HS) analysis was also carried out demonstrating that hydrogen-bonding and van der Waals interactions were the dominant interactions in the crystal packing. The urea groups form centrosymmetric dimers connected by intermolecular N–H•••O=C hydrogen bonds in a R 2 2 ( 8 ) motif. The 2,3-dichloro substitution has important effects on the packing stability, mostly via H•••Cl contacts, with H•••Cl/Cl•••H contributions of 26.1% of the intermolecular interactions." @default.
• W3191410802 created "2021-08-16" @default.
• W3191410802 creator A5013727977 @default.
• W3191410802 creator A5015860090 @default.
• W3191410802 creator A5023705098 @default.
• W3191410802 creator A5063163449 @default.
• W3191410802 date "2021-12-01" @default.
• W3191410802 modified "2023-10-07" @default.
• W3191410802 title "Intra- and intermolecular N–H•••O=C hydrogen bonds in 1-acyl urea compounds: Synthesis, X-ray structure, conformational and Hirshfeld surface analyses of 1-(2,3-dichlorophenyl)-3-pivaloylurea" @default.
• W3191410802 cites W1148031023 @default.
• W3191410802 cites W1152862260 @default.
• W3191410802 cites W1224803534 @default.
• W3191410802 cites W1723672461 @default.
• W3191410802 cites W1985232513 @default.
• W3191410802 cites W1987909343 @default.
• W3191410802 cites W2012488984 @default.
• W3191410802 cites W2013176211 @default.
• W3191410802 cites W2017398416 @default.
• W3191410802 cites W2019923102 @default.
• W3191410802 cites W2022366997 @default.
• W3191410802 cites W2038767330 @default.
• W3191410802 cites W2045185921 @default.
• W3191410802 cites W2049996223 @default.
• W3191410802 cites W2055766829 @default.
• W3191410802 cites W2071955309 @default.
• W3191410802 cites W2079363434 @default.
• W3191410802 cites W2080028754 @default.
• W3191410802 cites W2083945212 @default.
• W3191410802 cites W2104170538 @default.
• W3191410802 cites W2131350133 @default.
• W3191410802 cites W2144332006 @default.
• W3191410802 cites W2154358585 @default.
• W3191410802 cites W2166689829 @default.
• W3191410802 cites W2289151079 @default.
• W3191410802 cites W2315374233 @default.
• W3191410802 cites W2485706989 @default.
• W3191410802 cites W2590642972 @default.
• W3191410802 cites W2806664155 @default.
• W3191410802 cites W2807984726 @default.
• W3191410802 cites W2943811760 @default.
• W3191410802 cites W2950827460 @default.
• W3191410802 cites W2952584016 @default.
• W3191410802 cites W2981503757 @default.
• W3191410802 cites W2993714027 @default.
• W3191410802 cites W2995148416 @default.
• W3191410802 cites W4246229282 @default.
• W3191410802 doi "https://doi.org/10.1016/j.molstruc.2021.131271" @default.
• W3191410802 hasPublicationYear "2021" @default.
• W3191410802 type Work @default.
• W3191410802 sameAs 3191410802 @default.
• W3191410802 citedByCount "4" @default.
• W3191410802 countsByYear W31914108022022 @default.
• W3191410802 countsByYear W31914108022023 @default.
• W3191410802 crossrefType "journal-article" @default.
• W3191410802 hasAuthorship W3191410802A5013727977 @default.
• W3191410802 hasAuthorship W3191410802A5015860090 @default.
• W3191410802 hasAuthorship W3191410802A5023705098 @default.
• W3191410802 hasAuthorship W3191410802A5063163449 @default.
• W3191410802 hasConcept C112887158 @default.
• W3191410802 hasConcept C115624301 @default.
• W3191410802 hasConcept C126061179 @default.
• W3191410802 hasConcept C130188946 @default.
• W3191410802 hasConcept C166950319 @default.
• W3191410802 hasConcept C178790620 @default.
• W3191410802 hasConcept C185592680 @default.
• W3191410802 hasConcept C2779546866 @default.
• W3191410802 hasConcept C32909587 @default.
• W3191410802 hasConcept C71240020 @default.
• W3191410802 hasConcept C75079739 @default.
• W3191410802 hasConcept C8010536 @default.
• W3191410802 hasConceptScore W3191410802C112887158 @default.
• W3191410802 hasConceptScore W3191410802C115624301 @default.
• W3191410802 hasConceptScore W3191410802C126061179 @default.
• W3191410802 hasConceptScore W3191410802C130188946 @default.
• W3191410802 hasConceptScore W3191410802C166950319 @default.
• W3191410802 hasConceptScore W3191410802C178790620 @default.
• W3191410802 hasConceptScore W3191410802C185592680 @default.
• W3191410802 hasConceptScore W3191410802C2779546866 @default.
• W3191410802 hasConceptScore W3191410802C32909587 @default.
• W3191410802 hasConceptScore W3191410802C71240020 @default.
• W3191410802 hasConceptScore W3191410802C75079739 @default.
• W3191410802 hasConceptScore W3191410802C8010536 @default.
• W3191410802 hasLocation W31914108021 @default.
• W3191410802 hasOpenAccess W3191410802 @default.
• W3191410802 hasPrimaryLocation W31914108021 @default.
• W3191410802 hasRelatedWork W1991883810 @default.
• W3191410802 hasRelatedWork W2007892040 @default.
• W3191410802 hasRelatedWork W2034230510 @default.
• W3191410802 hasRelatedWork W2062301142 @default.
• W3191410802 hasRelatedWork W2081734998 @default.
• W3191410802 hasRelatedWork W2092928577 @default.
• W3191410802 hasRelatedWork W2385270671 @default.
• W3191410802 hasRelatedWork W2404645796 @default.
• W3191410802 hasRelatedWork W3146276033 @default.
• W3191410802 hasRelatedWork W4288489322 @default.
• W3191410802 hasVolume "1245" @default.
• W3191410802 isParatext "false" @default.
• W3191410802 isRetracted "false" @default.

• next