title: Synthesis, vibrational, NMR, quantum chemical and structure-activity relation studies of 2-hydroxy-4-methoxyacetophenone.
abstract: The stable geometry of 2-hydroxy-4-methoxyacetophenone is optimised by DFT/B3LYP method with 6-311++G(∗∗) and cc-pVTZ basis sets. The structural parameters, thermodynamic properties and vibrational frequencies of the optimised geometry have been determined. The effects of substituents (hydroxyl, methoxy and acetyl groups) on the benzene ring vibrational frequencies are analysed. The vibrational frequencies of the fundamental modes of 2-hydroxy-4-methoxyacetophenone have been precisely assigned and analysed and the theoretical results are compared with the experimental vibrations. 1H and 13C NMR isotropic chemical shifts are calculated and assignments made are compared with the experimental values. The energies of important MO's, the total electron density and electrostatic potential of the compound are determined. Various reactivity and selectivity descriptors such as chemical hardness, chemical potential, softness, electrophilicity, nucleophilicity and the appropriate local quantities are calculated.
authors.affiliation: Department of Chemistry, Kanchi Mamunivar Centre for Post-Graduate Studies, Puducherry 605 008, India. Electronic address: varjunftir@yahoo.com.
authors.forename: V
authors.initials: V
authors.lastname: Arjunan
authors.affiliation: Research and Development Centre, Bharathiar University, Coimbatore 641 046, India.
authors.forename: L
authors.initials: L
authors.lastname: Devi
authors.affiliation: Department of Chemistry, Kanchi Mamunivar Centre for Post-Graduate Studies, Puducherry 605 008, India.
authors.forename: R
authors.initials: R
authors.lastname: Subbalakshmi
authors.affiliation: Department of Chemistry, Rajiv Gandhi College of Engineering and Technology, Puducherry 605 402, India.
authors.forename: T
authors.initials: T
authors.lastname: Rani
authors.affiliation: School of Sciences and Humanities, Vel Tech University, Avadi, Chennai 600 062, India.
authors.forename: S
authors.initials: S
authors.lastname: Mohan
mesh_terms: D000098:Acetophenones / Q000138:chemical synthesis / Q000737:chemistry*; D000465:Algorithms; D002244:Carbon / Q000737:chemistry; D004583:Electrons; D006859:Hydrogen / Q000737:chemistry; D006860:Hydrogen Bonding; D009682:Magnetic Resonance Spectroscopy; D008968:Molecular Conformation; D010100:Oxygen / Q000737:chemistry; D011789:Quantum Theory; D012984:Software; D012997:Solvents / Q000737:chemistry; D017550:Spectroscopy, Fourier Transform Infrared; D013059:Spectrum Analysis, Raman; D055672:Static Electricity; D013329:Structure-Activity Relationship; D013499:Surface Properties; D013816:Thermodynamics; D014732:Vibration
chemical_list: D000098:Acetophenones; D012997:Solvents; C013638:paeonol; D002244:Carbon; D006859:Hydrogen; D010100:Oxygen
keywords: 2-Hydroxy-4-methoxyacetophenone; DFT; FT-Raman; FTIR; NMR