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

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[42] Infrared, 1H and 13C NMR spectral studies on di- and tri-substituted N-aryl amides, 2,6-X2C6H3NHCOCH3-iXi and 2,4,6-X3C6H2NHCOCH3-iXi (X = Cl or CH3 and i=0, 1, 2 or 3)
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[43] 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
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MAGNETIC RESONANCE IN CHEMISTRY, 2000, 38 (10) : 877 - 882
[44] Synthetic and 1H and 13C NMR spectral studies on N-(mono-substituted-phenyl)-acetamides and substituted acetamides, 2/3/4-YC6H4NH-CO-CH3-iXi (Y = CH3, F, Cl, Br, NO2;: X = Cl, CH3;: i=0, 1, 2, 3)
Gowda, Basavalinganadoddy Thimme
Shilpa
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ZEITSCHRIFT FUR NATURFORSCHUNG SECTION A-A JOURNAL OF PHYSICAL SCIENCES, 2006, 61 (10-11): : 595 - 599
[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
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JOURNAL OF MOLECULAR STRUCTURE, 2015, 1095 : 112 - 124
[46] 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.
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ZEITSCHRIFT FUR NATURFORSCHUNG SECTION A-A JOURNAL OF PHYSICAL SCIENCES, 2006, 61 (10-11): : 600 - 606
[47] Novel pentafulvalene derivatives:: synthesis, crystal structures, 1H and 13C NMR chemical shift assignments of trans- and cis-isomers of bis-2,2′-(4,5,6,7-tetrachloro-8,8-dimethoxy-3a,4,7,7a-tetrahydro-4,7-methanoindan-1,3a- dienylidene)
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NEW JOURNAL OF CHEMISTRY, 1999, 23 (07) : 691 - 693
[48] Infrared, 1H and 13C NMR spectra of N,N-dichloroarylsulphonamides, 4-X-C6H4SO2NCl2 (X = H, CH3, C2H5, F, Cl or Br) and i-X, j-YC6H3SO2 NCl2 (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)
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ZEITSCHRIFT FUR NATURFORSCHUNG SECTION A-A JOURNAL OF PHYSICAL SCIENCES, 2003, 58 (9-10): : 563 - 568
[49] 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)
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