Observation of Diastereotopic Signals in 15N NMR Spectroscopy

被引：5

作者：

Alkorta, Ibon ^{[1
]}

Dardonville, Christophe ^{[1
]}

Elguero, Jose ^{[1
]}

机构：

[1] CSIC, Inst Quim Med, E-28006 Madrid, Spain

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2015年 / 54卷 / 13期

关键词：

analytical methods; chirality; density functional calculations; nitrogen heterocycles; NMR spectroscopy; MULTINUCLEAR MAGNETIC-RESONANCE; CHEMICAL-SHIFTS; METHYL-GROUPS; LIGANDS; F-19; C-13; STEREOCHEMISTRY; ROTATION; SPECTRA; ATOMS;

D O I：

10.1002/anie.201412144

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The first example in the literature of a compound showing anisochronous N-15 atoms resulting from diastereotopicity is described. Racemic 1,3-dimethyl-2-phenyloctahydro-1H-benzimidazole was prepared and studied by H-1, C-13 and N-15 NMR spectroscopy. If convenient conditions were used (monitored by theoretical calculations of (2)J(N-H) spin-spin coupling constants), two N-15 NMR signals were observed and corresponded to the diastereotopic atoms. GIAO/density-functional calculations of chemical shifts were not only in good agreement with the experimental values but also served as prediction tools. This study suggests that N-15 NMR spectroscopy could be used to probe chirality.

引用

页码：3997 / 4000

页数：4

共 50 条

[31] The production of recombinant 15N, 13C-labelled somatostatin 14 for NMR spectroscopy
Nespovitaya, Nadezhda
Barylyuk, Konstantin
Eichmann, Cedric
Zenobi, Renato
Riek, Roland
PROTEIN EXPRESSION AND PURIFICATION, 2014, 99 : 78 - 86
[32] 13C and 15N NMR spectroscopy as a tool in soil organic matter studies
Kogel-Knabner, I
GEODERMA, 1997, 80 (3-4) : 243 - 270
[33] 1H, 13C and 15N NMR spectroscopy and tautomerism of nitrobenzotriazoles
Larina, Lyudmila I.
Milata, Viktor
MAGNETIC RESONANCE IN CHEMISTRY, 2009, 47 (02) : 142 - 148
[34] Defining the orientation of the 15N shielding tensor using 15N NMR relaxation data for a protein in solution
Boyd, J
Redfield, C
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (37) : 9692 - 9693
[35] 15N NMR investigation of the hydrolysis of bismaleimide polymers
Curliss, D.B.
Cowans, B.A.
Caruthers, J.M.
Polymer Preprints, Division of Polymer Chemistry, American Chemical Society, 1993, 34 (02):
[36] Solvent effects on 15N NMR coordination shifts
Kleinmaier, Roland
Arenz, Sven
Karim, Alavi
Carlsson, Anna-Carin C.
Erdelyi, Mate
MAGNETIC RESONANCE IN CHEMISTRY, 2013, 51 (01) : 46 - 53
[37] Synthesis and 15N NMR Signal Amplification by Reversible Exchange of [15N]Dalfampridine at Microtesla Magnetic Fields
Chukanov, Nikita V.
Salnikov, Oleg G.
Trofimov, Ivan A.
Kabir, Mohammad S. H.
Kovtunov, Kirill V.
Koptyug, Igor V.
Chekmenev, Eduard Y.
CHEMPHYSCHEM, 2021, 22 (10) : 960 - 967
[38] Vibrational and 15N NMR probe for nucleic acids
Gai, Xin
Fenlon, Edward E.
Brewer, Scott H.
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2010, 239
[39] OBSERVATION OF A 9.15 MEV DOUBLET LEVEL IN 15N FROM A STUDY OF 14N(N,GAMMA)15N REACTION
GREENWOOD, RC
PHYSICS LETTERS B, 1968, B 27 (05) : 274 - +
[40] Syntheses of (2′)3′-15N-Amino-(2′)3′-deoxyguanosine and determination of their pKa values by 15N NMR spectroscopy
Dai, Qing
Lea, Charles R.
Lu, Jun
Piccirilli, Joseph A.
ORGANIC LETTERS, 2007, 9 (16) : 3057 - 3060

← 1 2 3 4 5 →