Browsing by Author "Aydin, A, Akkurt, M, Gul, HI, Mete, E, Sahin, E"

Now showing 1 - 5 of 5

Crystal structure of 3-(p-bromobenzoyl)-4-(p-bromophenyl)-1-isopropyl-4- piperidinol hydrochloride, C21H24Br2ClNO 2
(2013-10-25) Aydin A., Akkurt M., Gul H., Mete E., Sahin E.; Aydin, A, Akkurt, M, Gul, HI, Mete, E, Sahin, E
(Equation presentation) (Table presentation) Source of material Themixture of suitable ketone, paraformaldehyde and isopropylamine hydrochloride in 2:2:1 mol ratios was stirred and heated without solvent in an oil bath. Mono Mannich base, namely 1-pbromophenyl- 3-isopropylamino-1-propanone hydrochloride, and a piperidinol type compound, namely 3-(p-bromobenzoyl)- 4-(p-bromophenyl)-1- isopropylamino-4-piperidinol hydrochloride were produced in the reaction medium at the same time. Corresponding mono Mannich base of the title compound produced in the reactionmedium was removed from the reactionmedium to obtain the title compound. Solution of NaOH (5%) was added on residue. Reaction content was stirred at water bath at 313 K. Stirring was continued for 48 h observing the solidification of oily residue. Purification by crystallization from chloroform-hexane gave a white solid, yield 14 %, m.p. 485-487 K). Although solution of NaOH %5 was used, the elemental analysis result suggested that the salt with N-protonation was obtained. This information was confirmed by X Ray study. [Yield: 14 %, m.p.: 485-487 K]. 1H NMR (400 MHz, CDCl3, ppm) δ 1.44 (d, J = 6.6 Hz, 3H), 1.53 (d, J = 6.6 Hz, 3H), 1.94 (br d, J = 14.3 Hz, 1H), 2.84-2.91 (m, 1H), 3.31-3.51 (m, 5H), 5.01 (d, J = 2.6 Hz, 1H, OH), 5.78 (dd, J = 12.1, 3.7 Hz, 1H), 7.36 (d, J = 8.4 Hz, 2H), 7.43 (d, J = 8.4 Hz, 2H), 7.61 (d, J = 8.4 Hz, 2H), 8.02 (d, J = 8.4 Hz, 2H); 13C NMR (100 MHz, CDCl3, ppm) δ 16.3, 17.6, 36.4, 43.7, 46.1, 47.7, 58.5, 72.2, 122.0, 126.6, 130.9, 131.3, 132.0, 132.3, 133.0, 143.2, 201.2; MS (EI) m/z: 482.4; IR (KBr,cm-1): 1675 (CO). Calcd. for C21H24Br2ClNO2 (517.68): C, 48.72; H, 4.67; N, 2.71. Found: C, 48.74; H, 4.70; N, 2.83. (Table presentation) Discussion The piperidinium ring (N1/C4-C8), (Fig.1), adopts a chair conformation with the puckering parameters [1] of QT = 0.593(4) Å, θ = 174.4(4)°, φ = 179(4)°. The dihedral angle between the benzene rings (C9-C14 and C16-C21) is 61.4(2)°. The O1-C15-C7-C6, O2-C6-C7-C15, C1-C2-N1-C8 and C3-C2-N1-C8 torsion angles are -74.3(5), -56.0(5), 159.8(4) and -74.4(5)°, respectively. The Br-C1 bond lengths are 1885(5) and 1.895(5) Å and the C6-O2 bond length is 1.429(5) Å. The C11-C12-Br1 and C9-C6-O2 bond angles are 119.2(4)° and 107.7(3)°, respectively. The values are in agreement with those in [2] (1.904(2) Å, 1.416(2) Å and 119.66(14)°, 105.76(14)°), respectively. An intramolecular O-H...O hydrogen bond forms a pseudo six-membered ring with S(6) ring motif [3]. The chloride counter anion is connected to the protonated nitrogen atom by a medium strong hydrogen bond. (Table presentation).
Crystal structure of 3-(thiophen-2-yl-carbonyl)-4-(thiophen-2-yl)-1- isopropyl-4-piperidinol, C17H21NO2S2
(2013-10-25) Aydin A., Akkurt M., Gul H., Mete E., Sahin E.; Aydin, A, Akkurt, M, Gul, HI, Mete, E, Sahin, E
(Equation presentation) (Table presentation) Source of material A mixture of a suitable ketone, paraformaldehyde and isopropylamine hydrochloride in the 2:2:1 ratio was stirred and heated without solvent in an oil bath. Mono Mannich base type, namely 1-(thiophen-2-yl)-3-isopropylamino-1-propanone hydrochloride, and a piperidinol type compound, namely 3-(thiophen-2-ylcarbonyl)- 4-(thiophen-2-yl)-1-isopropylamino-4-piperidinol hydrochloride were produced in the reaction medium at the same time. Corresponding mono Mannich base of the title compound produced in the reaction medium together with the title compound was removed from the reaction. A solution of NaOH (5%) was added on the residue. The reaction content was stirred at water bath at 313 K. Stirring was continued for 48 h observing the solidification of oily residue. Compound (I) was purified by crystallization from methanol-ether. [Yield: 11 %, mp.: 416-417 K]. 1H-NMR (400 MHz, CDCl3, ppm) δ: 1.09 (d, J = 6.2 Hz, 6H), 2.00-2.05 (m, 2H), 2.75-2.98 (m, 5H), 4.04 (br d, J = 8.8 Hz, 1H), 5.44 (s, 1H, OH), 6.82 (dd, J = 4.6, 3.3Hz, 1H), 6.91 (br d, J = 3.3 Hz, 1H), 7.07 (d, J = 4.6 Hz, 1H), 7.12 (dd, J = 4.8, 3.7 Hz, 1H), 7.67 (d, J = 4.8 Hz, 1H), 7.80 (d, J = 3.7 Hz, 1H); 13C-NMR (100 MHz, CDCl3, ppm) δ: 18.6, 18.8, 41.6, 44.4, 49.1, 54.4, 54.9, 72.9, 122.2, 123.9, 127.0, 128.8, 133.5, 135.8, 143.8, 153.4, 196.9; MS (EI) m/z: 335.2; IR (KBr,cm-1): 1635 (CO). Calcd. for C17H21NO2S2 (335.48): C, 60.86; H, 6.31; N, 4.18; S, 19.12. Found: C, 60.55; H, 6.55; N, 4.18; S, 19.47. Experimental details All H atoms were positioned geometrically and treated as riding on their parent atoms, with O-H = 0.82 (hydroxyl), C-H = 0.93 (aromatic), 0.97 Å (methylene), respectively, and with Uiso(H) = 1.5Ueq(C, O) for methyl and hydroxyl andUiso(H) = 1.2Ueq(C) for the others. One of the two thiophene rings is disordered over two positions, corresponding to rotation of approximately 180° about the single C-C bond, with site occupancy factors of 0.676(3) and 0.324(3). The atoms of the isopropyl group are also disordered over two positions [occupancies = 0.605(8):0.395(8)]. Discussion In the title structure (Fig.) the piperidine ring (N1/C6-C10) adopts a chair conformation which is evident from the puckering parameters [1]: QT= 0.585(4) Å, θ = 178.0(4)° and φ = 162(10)°, respectively. The plane of the thiophene ring (S1/C1-C4) makes dihedral angles of and 81.9(3)° and 79.0(6)°, respectively, with the planes of the major and minor components (S2A/C11/C12A-C14A and S2B/C11/C12B-C14B) of the disordered thiophene ring, while these disordered thiophene rings form a dihedral angle of 8.0(6)° with each other. The bond lengths and angles are within normal ranges and comparable with those observed in the similar structures [2]. The C14A-S2A and C1-S1 bond lengths are 1.690(8) Å, and 1.682(5) Å, respectively. The C14A-S2A-C11 and C1-S1-C4 bond angles are 93.0(3)° and 91.9(2)°, respectively and the values are in agreement with those in [3] (1.697(2) Å, 1.704(2) Å and 93.6(1)°, 92.2(1)°), respectively. The molecular conformation is stabilized by intramolecular O2-H2A...O1 hydrogen bond, with a S(6) ring motif [4]. Semiempirical AM1 calculations of the title structure were carried out with WinMopac 7.2 software [5, 6]. The dihedral angle between the thiophene rings is 49.08° and is different from that in the x-ray result. The dipole moment, the HOMO and LUMO energy levels are calculated as about 2.530 Debye, -9.1202 and -0.0523 eV, respectively.Wemay state that the theoretical calcu- lation supports the suggestion that the present intra and intermolecular interactions influence the molecular geometry. (Table presentation).
N-(2-Benzoylethyl)propan-2-aminium chloride
(2012-09-01) Aydn A., Akkurt M., Gul H.I., Mete E., Sahin E.; Aydin, A, Akkurt, M, Gul, HI, Mete, E, Sahin, E
In the title salt, C12H18NO+· Cl-, N - H⋯Cl interactions between the free chloride anions and the organic cations connect the molecules into hydrogen-bond dimers, forming a R22(8) motif. The dimers are linked by C - H⋯O hydrogen bonds into chains extending along [301]. The carbonyl group is co-planar with the phenyl ring [C - C - C=O torsion angle = -3.3 (7)°]. The side chain has an E conformation.
N-[2-(4-bromobenzoyl)ethyl]isopropylaminium chloride
(2012-01-01) Aydin A., Akkurt M., Gul H., Mete E., Sahin E.; Aydin, A, Akkurt, M, Gul, HI, Mete, E, Sahin, E
The crystal structure of the title compound, C 12H 17BrNO +·-Cl -, is stabilized by N-H···Cl and C-H···O hydrogen bonds, forming a three-dimensional network. The interactions framework is completed by C-H···π contacts between a methylene group and the benzene ring of a symmetry-related molecule.
N-[2-(4-Methylbenzoyl)ethyl]propan-2-aminium chloride
(2012-09-01) Aydn A., Akkurt M., Gul H.I., Mete E., Sahin E.; Aydin, A, Akkurt, M, Gul, HI, Mete, E, Sahin, E
In the title compound, C13H20NO+· Cl-, the protonated amino N atom is hydrogen bonded to the chloride anion. N - H⋯Cl hydrogen bonds link the anions and cations into dimers, which are connected by C - H⋯O hydrogen bonds, forming supra-molecular chains extending along [100].