2-Benzoyl-1,1-diethyl-3-phenyl-guanidine

Area of Science:

• Crystallography
• Organic Chemistry
• Supramolecular Chemistry

Background:

• Tetrasubstituted guanidines are a significant class of organic compounds with diverse applications.
• Molecular conformation and intermolecular interactions dictate the bulk properties of crystalline solids.
• Understanding hydrogen bonding patterns is crucial for predicting crystal packing and reactivity.

Purpose of the Study:

• To investigate the crystal structure and molecular conformation of a specific tetrasubstituted guanidine derivative.
• To elucidate the role of intramolecular and intermolecular hydrogen bonding in the observed structure.
• To analyze the dihedral angles between key functional groups and their implications.

Main Methods:

• Single-crystal X-ray diffraction was employed to determine the three-dimensional structure.
• Analysis of torsion angles and dihedral angles to quantify molecular geometry.
• Identification and analysis of intermolecular and intramolecular hydrogen bonding interactions.

Main Results:

• The guanidine and carbonyl groups were found to be non-planar, with significant torsion angles around the N=C bonds.
• Absence of an intramolecular N-H⋯O hydrogen bond, which is typically observed in similar compounds.
• Formation of centrosymmetric dimers through intermolecular N-H⋯O hydrogen bonds in the crystal lattice.
• Specific dihedral angles were measured between the guanidine plane and the phenyl/benzoyl rings.

Conclusions:

• The non-planar conformation is attributed to the lack of stabilizing intramolecular hydrogen bonds.
• Intermolecular hydrogen bonding plays a key role in the crystal packing, leading to dimer formation.
• The study provides insights into the structure-property relationships of tetrasubstituted guanidines.