3-Chloro-N,N-di-methyl-propan-1-aminium chloride

Area of Science:

• Organic Chemistry
• Crystallography
• Computational Chemistry

Background:

• The study investigates the molecular salt C5H13NCl+·Cl-.
• Understanding conformational preferences and crystal packing is crucial in molecular science.

Purpose of the Study:

• To elucidate the conformational behavior of the organic cation in C5H13NCl+·Cl-.
• To analyze the factors contributing to the observed crystal symmetry.

Main Methods:

• Density Functional Theory (DFT) geometry optimizations were employed.
• X-ray crystallography was used to determine the crystal structure.

Main Results:

• The organic cation exhibits a gauche effect, stabilizing the gauche conformation via C-H bond electron donation to the C-Cl antibonding orbital.
• DFT calculations confirmed C-Cl bond lengthening in the gauche conformation compared to the anti conformation.
• The crystal structure displays a higher point group symmetry (4) than the cation, attributed to a supramolecular square arrangement of four cations.

Conclusions:

• The gauche effect plays a significant role in the conformational preference of this organic cation.
• Supramolecular assembly in the crystal lattice leads to emergent symmetry higher than that of the individual molecular cation.