Crystal structure of 1-acetyl-3-(4-methylphenyl)-5-phenyl-4,5-dihydro-1 H -pyrazole
- PDF / 198,999 Bytes
- 3 Pages / 612 x 792 pts (letter) Page_size
- 22 Downloads / 139 Views
TRUCTURE OF ORGANIC COMPOUNDS
Crystal Structure of 1Acetyl3(4methylphenyl)5phenyl4,5 dihydro1Hpyrazole1 . . H. Bülbüla, *, F. Tinmazb, N. Degea, I . Özer I lhanb, and E. Sari p i narb
a
Department of Physics, Faculty of Arts and Sciences, Ondokuz May is University, 55200, Samsun, Turkey b Department of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey email: [email protected] Received November 25, 2013; in final form, May 15, 2014
Abstract—In the title compound, C18H18N2O, the whole molecule is not planar but the phenyl ring systems are planar individually. The central pyrazole ring system is twisted with puckering parameters Q = 0.1610(18) Å and ϕ = 82.2(6)°. The crystallographic structure is stabilized by C–H···N type intramolecular hydrogen bond, generating ring motif R(5). DOI: 10.1134/S106377451408001X
INTRODUCTION Heterocyclic compounds are well known for their wide range of biological applications [1–5] out of which pyrazolines occupy unique position due to dominant applications. Pyrazolines are known to pos sess antimicrobial [6, 7], antitubercular [8], antiviral [9], anti HIV [10], molluscicidal [11] and cerebropro tective [12] properties etc. One of the important appli cations of pyrazoline is the use of pyrazolines as a flu orescent brightening agent [13]. Pyrazolines are also acting as hole transporting material in OELD (organic electroluminescent device) because of formation of p–π conjugated system due to one of the nitrogen atom. Pyrazolines have variety of methods for its syn thesis but one of the popular methods is of Fischer and Knoevenagel i.e. the reaction of α,βunsaturated ketones with phenyl hydrazine in acetic acid under refluxing condition [14–16].
EXPERIMENTAL Synthesis. A mixture of Chalcone (1.4 g, 6.73 mmol) and acetohydrazide (0.5 g, 6.73 mmol) dissolved in ethanolic sodium hydroxide (20 mL) was refluxed for 5 h. The mixture was poured into icewater. The pre cipitate obtained was filtered off, washed and recrys tallized from cyclohexane. The completion of the reaction was monitored by TLC (Fig. 1). The yield 1.42 g (80%), m.p. 392–393 K. IR (ATR) cm–1: 3061.78, 3033.60 (aromatic –CH), 2917.76 (alifatic –CH), 1659.24 (C=O of acetyl), 1608.78 (C=N of pyrazoline ring); 1HNMR (δ, ppm): 5.62, 5.61, 5.59, 5.58 (t, 1H, –CH); t1 3.79, 3.76, 3.74, 3.71, t2 3.19, 3.18, 3.15, 3.14 (2t, 2H, –CH2); 2.51, 2.45, (s, 6H, –CH3); 7.67–7.24 (m, 12H, ArR); 13CNMR (δ, ppm): 21.58, 21.53 (–CH3), 42.43 (–CH2), 59.88 (–CH), (125.26, 125.58, 126.57, 126.81, 127.62, 127.82,
H3C
H3C
O C CH + H2N NH HC C O CH3
C CH3CH2OH NaOH
CH2
N N O
C H
C CH3
Fig. 1. Chemical diagram of 1acetyl3(4methylphenyl)5phenyl4,5dihydro1Hpyrazole.
1
The article is published in the original.
1071
1072
BÜLBÜL et al.
Table 1. Crystallographic characteristics and the Xray data collection and structurerefinement parameters for C18H18N2O System, sp. gr., Z
Monoclinic, P21/c
a, b, c, Å
14.8350(8), 10.9443(4), 9.7589(5)
β, deg
1501.87(12)
Dx , g cm–3
1.231
Radi
Data Loading...
