Related Experiment Video
Updated: Mar 29, 2026

Construction and Systematical Symmetric Studies of a Series of Supramolecular Clusters with Binary or Ternary Ammonium Triphenylacetates
Published on: February 15, 2016
Crystal structure of {[2-hy-droxy-2-(3-meth-oxy-phen-yl)cyclo-hex-yl]meth-yl}di-methyl-ammonium benzoate
S N Sheshadri1, P Nagendra2, B P Siddaraju3
1Department of Chemistry, GSSS Institute of Engineering Technology for Women, Mysuru 570 016, India.
Abstract:
The title compound, C16H26NO2 (+)·C7H5O2 (-), is a benzoate salt of the painkiller Tramadol. The six-membered cyclo-hexane ring of the cation adopts a slightly distorted chair conformation and carries OH and 3-meth-oxy-phenyl substituents at the 2-position and a protonated methyl-aza-niumylmethyl group at the 3-position. In addition, a weak intra-molecular C-H⋯O hydrogen bond is observed in the cation. In the crystal, weak O-H⋯O, N-H⋯O and C-H⋯O hydrogen bonds link the components into chains along [010]. A C-H⋯π contact is also observed.
Related Concept Videos
Stability of Substituted Cyclohexanes
The two chair conformations of cyclohexanes undergo rapid interconversion at room temperature. Both forms have identical energies and stabilities, each comprising equal amounts of the equilibrium mixture. Replacing a hydrogen atom with a functional group makes the two conformations energetically non-equivalent.
For example, in...
Conformations of Cyclohexane
The chair form is the most stable and derives its name from its resemblance to the “easy chair.” In the chair conformation, two carbon atoms are arranged out-of-plane — one above and one below, minimizing the torsional strain. In the chair form, the bond angle is very close to the ideal...
Structures of Carboxylic Acid Derivatives
Carboxylic acid derivatives contain an acyl group attached to a heteroatom such as chlorine, oxygen, or nitrogen. The carbonyl carbon and oxygen are both sp2-hybridized with an unhybridized p orbital.
The three sp2 orbitals of the carbonyl carbon form three σ bonds, one each with the carbonyl oxygen, the α carbon, and the heteroatom, whereas the other two sp2 orbitals of the carbonyl oxygen are occupied by the lone pairs. Further, the unhybridized p...
Structure of Amines
Chair Conformation of Cyclohexane
The hydrogen atoms linked to carbons are arranged in two different axial and equatorial orientations to achieve this...
Aromatic Hydrocarbon Cations: Structural Overview
Removing one hydrogen from the intervening CH2 group...

