A new chalcone structure of (E)-1-(4-Bromophenyl)-3-(napthalen-2-yl)prop-2-en-1-one: Synthesis, structural characterizations, quantum chemical investigations and biological evaluations.
The structure of (E)-1-(4-Bromophenyl)-3-(napthalen-2-yl)prop-2-en-1-one (C19H13BrO) crystallized in the triclinic system of P-1 space group. The unit cell dimensions are: a=5.8944 (9)Å, b=7.8190 (12)Å, c=16.320 (2)Å, α=102.4364 (19)°, β=95.943 (2)°, γ=96.274 (2)° and Z=2. The physical properties of this compound was determined by the spectroscopic methods (FTIR and (1)H and (13)C NMR). Quantum chemical investigations have been employed to investigate the structural and spectral properties. The molecular structure, vibrational assignments, (1)H and (13)C NMR chemical shift values, non-linear optical (NLO) effect, HOMO-LUMO analysis and natural bonding orbital (NBO) analysis were calculated using HF and DFT/B3LYP methods with 6-311++G(d,p) basis set in the ground state. The results show that the theoretical calculation of the geometrical parameters, vibrational frequencies and chemical shifts are comparable with the experimental data. The crystal structure is influenced and stabilized by weak C-H⋯π interactions connecting the molecules into infinite supramolecular one dimensional ladder-like arrangement. Additionally, this compound is evaluated for their antibacterial activities against gram positive and gram negative strains using a micro dilution procedure and shows activities against a panel of microorganisms.
X-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia.
Kaliyaperumal
K
Thanigaimani
X-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia.
Suhana
S
Arshad
X-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia.
Nuridayanti Che
NC
Khalib
X-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia. Electronic address: arazaki@usm.my.
Ibrahim Abdul
IA
Razak
Research Department of Physics, Government Arts College, Ariyalur 621713, Tamil Nadu, India.
C
C
Arunagiri
Research Department of Chemistry, Seethalakshmi Ramaswami College, Tiruchirappalli 620 002, Tamil Nadu, India.
A
A
Subashini
School of Biological Sciences, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia.
Shaida Fariza
SF
Sulaiman
School of Biological Sciences, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia.
Nurul Shafiqah
NS
Hashim
School of Biological Sciences, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia.
Kheng Leong
KL
Ooi
D000975:Antioxidants / Q000494:pharmacology; D001419:Bacteria / Q000187:drug effects; D002247:Carbon Isotopes; D002599:Chalcone / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D047188:Chalcones / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D018360:Crystallography, X-Ray; D006244:Hardness; D006859:Hydrogen; D006860:Hydrogen Bonding; D008826:Microbial Sensitivity Tests; D008958:Models, Molecular; D008968:Molecular Conformation; D014442:Monophenol Monooxygenase / Q000037:antagonists & inhibitors; D009281:Naphthalenes / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D017711:Nonlinear Dynamics; D055620:Optical Phenomena; D011789:Quantum Theory; D017550:Spectroscopy, Fourier Transform Infrared; D013816:Thermodynamics; D014732:Vibration; D015003:Yeasts / Q000187:drug effects
C000610505:1-(4-bromophenyl)-3-(napthalen-2-yl)prop-2-en-1-one; D000975:Antioxidants; D002247:Carbon Isotopes; D047188:Chalcones; D009281:Naphthalenes; D002599:Chalcone; D006859:Hydrogen; D014442:Monophenol Monooxygenase
Biological evaluations; Chalcone; Density functional; Hartree–Fock; Molecular structure; Spectroscopic analyses