N-(4-Chloro-2-methyl-phen-yl)maleamic acid

Area of Science:

• Crystallography and Molecular Structure
• Organic Chemistry
• Supramolecular Chemistry

Background:

• Understanding molecular conformation and intermolecular interactions is crucial in chemistry.
• The specific arrangement of functional groups dictates a compound's physical and chemical properties.
• Hydrogen bonding plays a significant role in crystal engineering and material properties.

Purpose of the Study:

• To elucidate the detailed molecular structure of the title compound, C(11)H(10)ClNO(3).
• To investigate the conformational preferences of the amide and acid groups.
• To analyze the role of intramolecular and intermolecular hydrogen bonding in crystal packing.

Main Methods:

• Single-crystal X-ray diffraction analysis was employed to determine the molecular and crystal structure.
• Conformational analysis of key functional groups (amide, acid) was performed.
• Identification and characterization of hydrogen bonding networks (intra- and intermolecular) were conducted.

Main Results:

• The molecular structure exhibits a syn conformation of the N-H bond relative to the ortho-methyl group.
• A rare anti positioning of the C=O and O-H bonds in the acid group was observed, stabilized by an intramolecular hydrogen bond.
• The oxobutenoic acid core is significantly twisted (31.65°) out of the phenyl ring plane, and molecules form infinite chains via N-H⋯O hydrogen bonds.

Conclusions:

• The study reveals unique conformational features driven by intramolecular hydrogen bonding.
• The observed crystal structure highlights the role of specific hydrogen bond donors and acceptors in directing molecular assembly.
• Findings contribute to the understanding of structure-property relationships in substituted aromatic compounds.