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NMR Spectroscopy of Benzene Derivatives

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Simple unsubstituted benzene has six aromatic protons, all chemically equivalent. Therefore, benzene exhibits only a singlet peak at δ 7.3 ppm in the 1H NMR spectrum. The observed shift is far downfield because the aromatic ring current strongly deshields the protons. Any substitution on the benzene ring makes the aromatic protons nonequivalent, and the protons split each other. The peak is, therefore, no longer a singlet and the splitting pattern and their associated coupling constants depend...

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The simplest aromatic amine is phenylamine, which contains an –NH2 functionality directly attached to an aromatic ring. The name aniline is designated for this skeleton. As shown in Figure 1, the common names of the functionalized anilines involve prefixes ortho-, meta-, and para- to indicate the substitution position. Different functionalized aniline derivatives also have notable trivial names.

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Summary

This study details the molecular structure of C(15)H(15)NO, revealing specific bond conformations and spatial arrangements. The research highlights how hydrogen bonds influence the crystal packing, forming extended molecular chains.

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Area of Science:

Crystallography
Organic Chemistry
Molecular Structure

Background:

Understanding the precise three-dimensional arrangement of atoms in organic molecules is crucial for predicting their chemical behavior and physical properties.
The title compound, C(15)H(15)NO, presents an interesting case for structural analysis due to its amide linkage and substituted aromatic rings.

Purpose of the Study:

To elucidate the detailed molecular conformation and crystal structure of the title compound, C(15)H(15)NO.
To investigate the intermolecular interactions, specifically hydrogen bonding, that govern the compound's solid-state architecture.

Main Methods:

Single-crystal X-ray diffraction was employed to determine the atomic coordinates and confirm the molecular geometry.
Analysis of bond lengths, bond angles, and dihedral angles provided insights into the molecule's conformation.

Main Results:

The N-H and C=O bonds of the amide group were found to be in a trans conformation.
The amide oxygen atom is syn to the ortho-methyl group on the benzoyl ring.
Significant tilting of the amide group (59.96°) and a large dihedral angle between the aromatic rings (81.44°) were observed.
N-H⋯O hydrogen bonds were identified, leading to the formation of infinite chains along the c-axis.

Conclusions:

The crystal structure of C(15)H(15)NO is characterized by specific conformational preferences of the amide group and its orientation relative to the aromatic rings.
Intermolecular N-H⋯O hydrogen bonding plays a key role in organizing the molecules into one-dimensional chains, influencing the overall crystal packing.