(S)-2-Carb-oxy-ethyl l-cysteinyl sulfone

Area of Science:

• Crystallography
• Supramolecular Chemistry
• Computational Chemistry

Background:

• Understanding the solid-state behavior of zwitterionic compounds is crucial for materials science and drug design.
• The title compound, (2S)-2-aza-niumyl-3-[(2-carboxy-ethane)-sulfonyl]propanoate (C6H11NO6S), presents a unique chemical structure with potential for interesting intermolecular interactions.

Purpose of the Study:

• To elucidate the crystal structure and intermolecular interactions of the title compound.
• To investigate the role of hydrogen bonding and electrostatic forces in stabilizing the crystal lattice.
• To estimate the total structure energy using computational methods.

Main Methods:

• Single-crystal X-ray diffraction analysis to determine the crystal structure.
• Analysis of hydrogen bonding networks and crystal packing.
• Density Functional Theory (DFT) calculations to estimate the total structure energy.

Main Results:

• The compound crystallizes in the monoclinic space group P21 as an enantiopure zwitterion.
• Extensive multicentered intermolecular hydrogen bonding involving amino and carboxyl groups forms a diperiodic network.
• DFT calculations estimated the total structure energy to be Etotal = -333.5 kJ mol-1, highlighting the dominance of electrostatic forces.

Conclusions:

• The crystal structure is stabilized by a robust hydrogen-bonding network and significant electrostatic interactions.
• The findings provide insights into the solid-state behavior of zwitterionic molecules with sulfonyl and carboxyl functionalities.
• This study contributes to the understanding of structure-property relationships in organic crystals.