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Updated: Jun 1, 2026
07:06
Continuous Flow Chemistry: Reaction of Diphenyldiazomethane with p-Nitrobenzoic Acid
Published on: November 15, 2017
2-(2,7-Dimeth-oxy-1-naphtho-yl)benzoic acid.
Daichi Hijikata1, Kosuke Nakaema, Shoji Watanabe
1Department of Organic and Polymer Materials Chemistry, Tokyo University of Agriculture & Technology, Koganei, Tokyo 184-8588, Japan.
Summary
This study details the molecular structure of a novel organic compound, C(20)H(16)O(5), revealing specific dihedral angles between its aromatic rings and carbonyl groups. Crystal structure analysis identified key intermolecular and intramolecular hydrogen bonds stabilizing the molecule.
Area of Science:
- Organic Chemistry
- Crystallography
- Molecular Structure
Background:
- Understanding the three-dimensional arrangement of atoms in organic molecules is crucial for predicting their properties and reactivity.
- Aromatic systems and carbonyl groups are common functional groups in organic chemistry, and their relative orientation influences molecular behavior.
Purpose of the Study:
- To elucidate the precise three-dimensional structure of the title compound, C(20)H(16)O(5).
- To quantify the dihedral angles between the naphthalene, benzene rings, and carbonyl groups.
- To identify and characterize the hydrogen bonding interactions that stabilize the crystal structure.
Main Methods:
- Single-crystal X-ray diffraction was employed to determine the molecular and crystal structure.
- Analysis of bond lengths, bond angles, and dihedral angles was performed.
- Identification of intermolecular and intramolecular hydrogen bonds was conducted.
Main Results:
- The dihedral angle between the naphthalene and benzene rings is 67.43°.
- Significant dihedral angles were observed between the carbonyl groups and the aromatic systems, ranging from 36.38° to 82.64°.
- The crystal structure is stabilized by intermolecular O-H⋯O and C-H⋯O hydrogen bonds, along with an intramolecular C-H⋯O hydrogen bond.
Conclusions:
- The study provides a detailed structural characterization of C(20)H(16)O(5), highlighting the spatial arrangement of its aromatic and carbonyl moieties.
- Hydrogen bonding plays a significant role in the crystal packing and stability of this compound.
- The determined structural parameters offer insights into the potential chemical and physical properties of this molecule.
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