Conformational flexibility in amidophosphoesters: a CSD analysis completed with two new crystal structures of (C 6 H 5 O) 2 P(O) X [ X = NHC 7 H 13 and N(CH 2 C 6 H 5 ) 2 ] - Archive ouverte HAL Accéder directement au contenu
Article Dans Une Revue Acta Crystallographica Section C : Structural Chemistry [2014-...] Année : 2020

Conformational flexibility in amidophosphoesters: a CSD analysis completed with two new crystal structures of (C 6 H 5 O) 2 P(O) X [ X = NHC 7 H 13 and N(CH 2 C 6 H 5 ) 2 ]

Arie van Der Lee
Banafsheh Vahdani Alviri
  • Fonction : Auteur
Mehrdad Pourayoubi
Abdul Ajees Abdul Salam
  • Fonction : Auteur
Marek Nečas
  • Fonction : Auteur
Arie van Der Lee
  • Fonction : Auteur
Akshara Chithran
  • Fonction : Auteur
Krishnan Damodaran

Résumé

The crystal structures of diphenyl (cycloheptylamido)phosphate, C 19 H 24 NO 3 P or (C 6 H 5 O) 2 P(O)(NHC 7 H 13 ), ( I ), and diphenyl (dibenzylamido)phosphate, C 26 H 24 NO 3 P or (C 6 H 5 O) 2 P(O)[N(CH 2 C 6 H 5 ) 2 ], ( II ), are reported. The NHC 7 H 13 group in ( I ) provides two significant hydrogen-donor sites in N—H...O and C—H...O hydrogen bonds, needed for a one-dimensional hydrogen-bond pattern along [100] in the crystal, while ( II ), with a (C 6 H 5 CH 2 ) 2 N moiety, lacks these hydrogen bonds, but its three-dimensional supramolecular structure is mediated by C—H...π interactions. The conformational behaviour of the phenyl rings in ( I ), ( II ) and analogous structures from the Cambridge Structural Database (CSD) were studied in terms of flexibility, volume of the other group attached to phosphorus and packing forces. From this study, synclinal (± sc ), anticlinal (± ac ) and antiperiplanar (± ap ) conformations were found to occur. In the structure of ( II ), there is an intramolecular C ortho —H...O interaction that imposes a + sc conformation for the phenyl ring involved. For the structures from the CSD, the + sc and ± ap conformations appear to be mainly imposed by similar C ortho —H...O intramolecular interactions. The large contribution of the C...H/H...C contacts (32.3%) in the two-dimensional fingerprint plots of ( II ) is a result of the C—H...π interactions. The differential scanning calorimetry (DSC) analyses exhibit peak temperatures ( T m ) at 109 and 81 °C for ( I ) and ( II ), respectively, which agree with the strengths of the intermolecular contacts and the melting points.

Domaines

Cristallographie

Dates et versions

hal-03544497 , version 1 (26-01-2022)

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Citer

Arie van Der Lee, Banafsheh Vahdani Alviri, Mehrdad Pourayoubi, Abdul Ajees Abdul Salam, Marek Nečas, et al.. Conformational flexibility in amidophosphoesters: a CSD analysis completed with two new crystal structures of (C 6 H 5 O) 2 P(O) X [ X = NHC 7 H 13 and N(CH 2 C 6 H 5 ) 2 ]. Acta Crystallographica Section C : Structural Chemistry [2014-..], 2020, 76 (1), pp.104-116. ⟨10.1107/S2053229619016619⟩. ⟨hal-03544497⟩
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