Linear free energy relationships of 13C NMR chemical shifts in 4-substituted phenyl-4,5-dihydrobenzo[f][1,4]oxazepin-3(2H)-ones(thiones)

被引：5

作者：

Agirbas, Hikmet ^{[1
]}

Kemal, Berat ^{[1
]}

机构：

[1] Kocaeli Univ, Dept Chem, TR-41300 Umuttepe, Izmit, Turkey

来源：

JOURNAL OF MOLECULAR STRUCTURE | 2013年 / 1053卷

关键词：

Benzoxazepines; C-13; NMR; Direct and extended polarizations; GIAO-DFT calculations; PERTURBATION-THEORY; DERIVATIVES; RESONANCE;

D O I：

10.1016/j.molstruc.2013.09.011

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

Linear free energy relationships (LFER) were applied to the C-13 NMR chemical shifts in 4-substituted phenyl-4,5-dihydrobenzo[f][1,4]oxazepin-3(2H)-ones(thiones). The correlation analysis for the substituent-induced chemical shifts (SCS) with inductive and resonance parameters (sigma, F and R) were carried out by using SSP (single substituent parameter) and DSP (dual substituent parameter). The presented calculation accounts satisfactorily for the polar and resonance substituent effects operating at benzoxazepine carbon atoms. Negative rho values were found for several correlations (reverse substituent effect). For a better understanding of the results, density functional theory (DFT) calculations were performed to determine the preferred geometry and to calculate the theoretical C-13 NMR chemical shifts. (C) 2013 Elsevier B.V. All rights reserved.

引用

页码：61 / 65

页数：5

共 50 条

[41] Synthetic, infrared, 1H and 13C NMR spectral studies on N-(2/3/4-substituted phenyl)-2,4-disubstituted benzenesulphonamides, 2,4-(CH3)2/2-CH3-4-Cl/2,4-Cl2C6H3SO2NH(i-XC6H4) (i-X = H, 2-CH3, 3-CH3, 4-CH3, 2-Cl, 3-Cl, 4-Cl, 4-F, 4-Br)
Basappa, Savitha M.
Gowda, Basavalinganadoddy Thimme
ZEITSCHRIFT FUR NATURFORSCHUNG SECTION A-A JOURNAL OF PHYSICAL SCIENCES, 2006, 61 (10-11): : 600 - 606
[42] Synthetic, infrared, 1H and 13C NMR spectral studies on N-(p-substituted phenyl)-p-substituted benzenesulphonamides, p-X′C6H4SO2NH-(p-XC6H4), where X′ or X = H, CH3, C2H5, F, Cl or Br
Gowda, BT
Jayalakshmi, KL
Shetty, M
ZEITSCHRIFT FUR NATURFORSCHUNG SECTION A-A JOURNAL OF PHYSICAL SCIENCES, 2004, 59 (4-5): : 239 - 249
[43] Dependence of 1H and 13C NMR chemical shifts on the PAH:FSO3H ratios for 4H-cyclopenta[def]phenanthrenium and pyrenium cations in SO2C1F.: Possible existence of cation-anion interactions and coexistence of PAHH+-PAH
Hollenstein, S
Laali, KK
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1999, (04): : 895 - 899
[44] 1H and 13C NMR study of 5-substituted-4-(arylidene)amino-2,4-dihydro-3H-1,2,4-triazole-3-thiones and 6-aryl-3-(D-gluco-pentitol-1-yl)-7H-1,2,4-triazolo[3,4-b] [1,3,4]thiadiazines
Zhang, Anjiang
Zhang, Lixue
Lei, Xinxiang
MAGNETIC RESONANCE IN CHEMISTRY, 2006, 44 (08) : 813 - 816
[45] Synthesis, spectral analysis (FT-IR, 1H NMR, 13C NMR and UV-visible) and quantum chemical studies on molecular geometry, NBO, NLO, chemical reactivity and thermodynamic properties of novel 2-amino-4-(4-(dimethylamino)phenyl)-5-oxo-6-phenyl-5,6-dihydro-4H-pyrano[3,2-c]quinoline-3-carbonitrile
Fatma, Shaheen
Bishnoi, Abha
Verma, Anil Kumar
JOURNAL OF MOLECULAR STRUCTURE, 2015, 1095 : 112 - 124
[46] LINEAR FREE-ENERGY RELATIONSHIPS IN THE THIOPHENE SERIES .4. ACID DISSOCIATION, REACTIVITY WITH DIAZODIPHENYLMETHANE IN METHANOL AND ANALYSIS OF C-13 AND O-17 NMR SUBSTITUENT CHEMICAL-SHIFTS OF SOME 5-SUBSTITUTED THIOPHENE-3-CARBOXYLIC ACIDS - CALCULATION OF THE SUBSTITUENT CONSTANTS IN THE THIOPHENE SERIES
SPINELLI, D
LAMARTINA, L
NOTO, R
CONSIGLIO, G
CHIMICHI, S
JOURNAL OF CHEMICAL RESEARCH-S, 1993, (08): : 300 - 301
[47] Complete assignment of the 1H and 13C NMR spectra of 2-phenyl-3H-naphtho[2,1-b][1,4]oxazin-3-one, 2-p-methoxyphenylnaphtho[1,2-d]oxazole and 2-phenylnaphtho[1,2-d]oxazole.: Concerted use of one- and two-dimensional NMR techniques
Márquez, A
Saitz, C
Cañete, A
Rodríguez, H
Jullian, C
MAGNETIC RESONANCE IN CHEMISTRY, 1998, 36 (06) : 449 - 453
[48] 3α,3′α-bis(n-acetoxyphenylcarboxy)-5β-cholan-24-oic acid ethane-1,2-diol diesters (n=2-4):: 13C NMR chemical shifts, variable-temperature and NOE 1H NMR measurements and MO calculations of novel bile acid-based dimers
Tamminen, J
Kolehmainen, E
Linnanto, J
Salo, H
Mänttäri, P
MAGNETIC RESONANCE IN CHEMISTRY, 2000, 38 (10) : 877 - 882
[49] Synthesis, XRD crystal structure, spectroscopic characterization (FT-IR, 1H and 13C NMR), DFT studies, chemical reactivity and bond dissociation energy studies using molecular dynamics simulations and evaluation of antimicrobial and antioxidant activities of a novel chalcone derivative, (E)-1-(4-bromopheny1)-3-(4-iodophenyl)prop-2-en-l-one
Zainuri, D. Alwani
Arshad, Suhana
Khalib, N. Che
Razak, I. Abdul
Pillai, Renjith Raveendran
Sulaiman, S. Fariza
Hashim, N. Shafiqah
Ooi, K. Leong
Armakovic, Stevan
Armakovic, Sanja J.
Panicker, C. Yohannan
Van Alsenoy, C.
JOURNAL OF MOLECULAR STRUCTURE, 2017, 1128 : 520 - 533
[50] Spectroscopic studies with N-chloroarylsulphonamides:: IR and 1H, 13C and 23Na NMR spectra of sodium salts of N-chloro-mono- and Di-substituted-benzenesulphonamides, 4-X-C6H4SO2NaNCl (X = H; CH3; C2H5; F; Cl; Br; I or NO2) and i-X,j-YC6H3SO2NaNCl (i-X,j-Y = 2,3-(CH3)2; 2,4-(CH3)2; 2,5-(CH3)2; 2-CH3,4-Cl; 2-CH3,5-Cl; 3-CH3,4-Cl; 2,4-Cl2 or 3,4-Cl2)
Gowda, BT
D'Souza, JD
Kumar, BHA
ZEITSCHRIFT FUR NATURFORSCHUNG SECTION A-A JOURNAL OF PHYSICAL SCIENCES, 2003, 58 (01): : 51 - 56

← 1 2 3 4 5 →