Molecular and crystal structure, lattice energy and DFT calculations of two 2′-(nitrobenzoyloxy)acetophenone isomers

Acta Crystallographica Section E: Crystallographic Communications

Georgii Bogdanov¹  Tatiana V. Timofeeva¹  Viktor Glebov¹  Jenna Bustos¹  Evgenii Oskolkov¹  John P. Tillotson² 

[1] Department of Chemistry, New Mexico Highlands University, Las Vegas, New Mexico, 87701, USA;School of Chemistry and Biochemistry, Georgia Institute of Technology, Atlanta, Georgia, 30332, USA;

关键词: 2′-(nitrobenzoyloxy)acetophenone isomers;    crystal structure;    molecular conformation;    dft calculations;    lattice energy;   

DOI  :  10.1107/S2056989020006295

来源: DOAJ

【 摘 要 】

The two isomers 2′-(4-nitrobenzoyloxy)acetophenone (systematic name: 2-acetylphenyl 4-nitrobenzoate) (I) and 2′-(2-nitrobenzoyloxy)acetophenone (systematic name: 2-acetylphenyl 2-nitrobenzoate) (II), both C15H11NO5, with para and ortho positions of the nitro substituent have been crystallized and studied. It is evident that the variation in the position of the nitro group causes a significant difference in the molecular conformations: the dihedral angle between the aromatic fragments in the molecule of I is 84.80 (4)°, while that in the molecule of II is 6.12 (7)°. Diffraction analysis revealed the presence of a small amount of water in the crystal of I. DFT calculations of the molecular energy demonstrate that the ortho substituent causes a higher energy for isomer II, while crystal lattice energy calculations show that the values are almost equal for two isomers.

【 授权许可】

Unknown