Simple and Effective Identification of Local 6π- and Global [4n+2] Aromaticity of Macrocyclic Conjugated Hydrocarbons by 1H/13C Chemical Shifts and the Corresponding Ring Current Effect

被引：0

作者：

Kleinpeter, Erich ^{[1
]}

Koch, Andreas ^{[1
]}

机构：

[1] Univ Potsdam, Chem Inst, Potsdam, Germany

来源：

MAGNETIC RESONANCE IN CHEMISTRY | 2024年 / 62卷 / 12期

关键词：

aromaticity; NICS; NMR; PAHs; TSNMRS; NICS; ANISOTROPY; VISUALIZATION; RESONANCE;

D O I：

10.1002/mrc.5482

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Structures, H-1/C-13 chemical shifts, and the ring current effects (spatial magnetic properties: through-space NMR shieldings [TSNMRSs]) of various pi-conjugated macrocyclic hydrocarbons and the corresponding charged analogues have been calculated at the B3LYP/6-311G(d,p) theory level using the GIAO perturbation method and employing the nucleus-independent chemical shift (NICS) characterization. The spatial magnetic properties (TSNMRS) are visualized as iso-chemical shielding surfaces (ICSSs) of various size and direction and together with especially the delta(H-1)/ppm chemical shifts employed to unequivocally qualify and quantify local 6 pi-aromaticity of individual benzenoid building blocks and the global ([4n + 2], n > 1) aromaticity of the macrocyclic ring.

引用

页码：861 / 870

页数：10

共 49 条

[31] An analysis of 1H, 13C and 15N NMR substituent chemical shifts in para- and meta-substituted (Z)-phenylhydrazones of 3-benzoyl-5-phenyl-1,2,4-oxadiazole
Mezzina, E
Spinelli, D
Lamartina, L
Buscemi, S
Frenna, V
Macaluso, G
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2002, 2002 (01) : 203 - 208
[32] 1H, 15N, and 13C chemical shift assignments of calcium-binding protein 1 with Ca2+ bound at EF1, EF3 and EF4
Saebomi Park
Congmin Li
James B. Ames
Biomolecular NMR Assignments, 2010, 4 : 159 - 161
[33] 1H, 15N, and 13C chemical shift assignments of calcium-binding protein 1 with Ca2+ bound at EF1, EF3 and EF4
Park, Saebomi
Li, Congmin
Ames, James B.
BIOMOLECULAR NMR ASSIGNMENTS, 2010, 4 (02) : 159 - 161
[34] 1H and 13C NMR spectral studies on N-(aryl)-substituted acetamides, C6H5NHCOCH3-iXi and 2/4-XC6H4NHCOCH3-iXi (where X = Cl or CH3 and i=0, 1, 2 or 3)
Gowda, BT
Usha, KM
Jayalakshmi, KL
ZEITSCHRIFT FUR NATURFORSCHUNG SECTION A-A JOURNAL OF PHYSICAL SCIENCES, 2003, 58 (12): : 801 - 806
[35] Experimental and quantum-chemical studies of 1H, 13C and 15N NMR coordination shifts in Pd(II) and Pt(II) chloride complexes with methyl and phenyl derivatives of 2,2′-bipyridine and 1,10-phenanthroline
Pazderski, Leszek
Tousek, Jaromir
Sitkowski, Jerzy
Kozerski, Lech
Szlyk, Edward
MAGNETIC RESONANCE IN CHEMISTRY, 2007, 45 (12) : 1045 - 1058
[36] 1H, 13C and 19F NMR data of N-substituted 6-(4-methoxyphenyl)-7H-pyrrolo[2,3-d]pyrimidin-4-amines in DMSO-d6
Sorum, Christopher
Simic, Nebojga
Sundby, Eirik
Hoff, Bard Helge
MAGNETIC RESONANCE IN CHEMISTRY, 2010, 48 (03) : 244 - 248
[37] 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
[38] NMR investigations of Clostridium pasteurianum rubredoxin.: Origin of hyperfine 1H, 2H, 13C and 15N NMR chemical shifts in iron-sulfur proteins as determined by comparison of experimental data with hybrid density functional calculations
Wilkens, SJ
Xia, B
Weinhold, F
Markley, JL
Westler, WM
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (19) : 4806 - 4814
[39] Synthetic, infrared, 1H and 13C NMR spectral studies on N-(2-/3-substituted phenyl)-4-substituted benzenesulphonamides, 4-X′C6H4SO2NH(2-/3-XC6H4)1 where X′ = H, CH3, C2H5, F, Cl or Br, and X = CH3 or Cl
Gowda, BT
Shetty, M
Jayalakshmi, KL
ZEITSCHRIFT FUR NATURFORSCHUNG SECTION A-A JOURNAL OF PHYSICAL SCIENCES, 2005, 60 (1-2): : 106 - 112
[40] The synthesis, NMR (1H, 13C, 119Sn) and IR spectral studies of some di- and tri-organotin(IV) sulfonates:: X-ray crystal structure of [(n-C4H9)2Sn(OSO2C6H4CH3-4)2•2H2O]
Kapoor, R
Gupta, A
Kapoor, P
Venugopalan, P
APPLIED ORGANOMETALLIC CHEMISTRY, 2003, 17 (08) : 607 - 615

← 1 2 3 4 5 →