N-Cyclohexylbenzamide

Abstract

The structure of the title compound, C13H17NO, features an anti disposition of the N—H and carbonyl groups. The amide group is twisted with respect to the benzene ring [N–C(=O)–C–C torsion angle = −30.8 (4)°]. In the crystal, C(4) chains propagating in [100] are formed by inter­molecular N–H⋯O hydrogen bonds. Weak C—H⋯π inter­actions link the chains into sheets.

Palladium-Mediated CO2 Extrusion Followed by Insertion of Isocyanates for the Synthesis of Benzamides: Translating Fundamental Mechanistic Studies To Develop a Catalytic Protocol

“…This is in contrast with the aggregation observed for the analogous thioamides we reported previously, where the Z conformer is exclusively observed, resulting in weakly dimeric structures due to short intermolecular N–H···S contacts . In this instance, the 2,6-dimethoxy groups on the benzamide prevent rotation of the phenyl plane, resulting in a much larger N1–C1–C2–C3 torsion angle (−71.0(4)°) relative to that in N -cyclohexylbenzamide (−30.8(4)°) …”

“…9 In this instance, the 2,6-dimethoxy groups on the benzamide prevent rotation of the phenyl plane, resulting in a much larger N1−C1−C2−C3 torsion angle (−71.0(4)°) relative to that in N-cyclohexylbenzamide (−30.8(4)°). 29 Condensed-Phase Mechanistic Studies under Ligand-Free Conditions Using Stoichiometric Pd Salts. To further probe whether the "ExIn" mechanism is operating in the condensed phase (eqs 3−5, Scheme 2), we have monitored the transformation of 2,6-dimethoxybenzoic acid to 5-Et by analyzing aliquots of reaction mixtures using 1 H NMR spectroscopy.…”