Complete NMR assignment of retinal and its related compounds

Complete and unambiguous ¹H and ¹³C NMR chemical shift assignments for all‐trans‐retinal, 13‐cis‐retinal, 11‐cis‐retinal and 9‐cis‐retinal (1–4) have been established by means of two‐dimensional COSY, HSQC, HMBC and NOESY spectroscopic experiments. Copyright © 2013 John Wiley & Sons, Ltd.     

Assignment of the 1H and 13C NMR signals of some hydroxyphenylcoumarins

The complete 1H and 13C NMR assignments of six hydroxyphenylcoumarins have been made using 1D and 2D NMR techniques, including COSY, HMQC and HMBC experiments.     

Assignment of the 1H and 13C NMR signals of some benzofurocoumarins

The complete 1H and 13C NMR assignment of four 6,7-benzo-fused furocoumarins (1-4) and three 3,4-benzo-fused furocoumarins (5-7) has been performed using 1D and 2D NMR techniques, including COSY, HMQC and HMBC experiments.     

Synthesis and complete assignment of the 1H and 13C NMR signals of some oxopyrancoumarin and oxofuropyrancoumarin derivatives

The synthesis of four pyranocoumarins starting from phloroglucinol and the complete (1)H and (13)C NMR assignment of seven pyranocoumarins has been performed using 1D and 2D NMR techniques including COSY, HMQC and HMBC experiments.     

Complete assignment of NMR data of 22 phenyl‐1H‐pyrazoles' derivatives

Complete assignment of ¹H and ¹³C NMR chemical shifts and J(¹H/¹H and ¹H/¹⁹F) coupling constants for 22 1‐phenyl‐1H‐pyrazoles' derivates were performed using the concerted application of ¹H 1D and ¹H, ¹³C 2D gs‐HSQC and gs‐HMBC experiments. All 1‐phenyl‐1H‐pyrazoles' derivatives were synthesized as described by Finar and co‐workers. The formylated 1‐phenyl‐1H‐pyrazoles' derivatives were performed under Duff's conditions. Copyright © 2011 John Wiley & Sons, Ltd.     

1H and 13C NMR spectral assignments of some natural abietane diterpenoids

An NMR study of 11 naturally occurring abietane diterpenoids is described. In addition to one‐dimensional NMR methods, including DPFGSE 1D‐NOE spectra, two‐dimensional shift‐correlated experiments [¹H,¹H COSY, ¹H,¹³C‐gHSQC ¹J(C,H) and ¹H,¹³C‐gHMBC ⁿJ(C,H) (n = 2 and 3)] were used for the complete and unambiguous ¹H and ¹³C chemical shift assignments of these substances. Copyright © 2003 John Wiley & Sons, Ltd.     

Synthesis of methoxybenzoflavones and assignments of their NMR data

A phytotoxic root exudate from Acroptilon repens was identified as 7,8‐benzoflavone, an inhibitor of cytochrome P450 1A2 and activator of cytochrome P450 3A4. The synthetic 5,6‐benzoflavone also is a potent phytotoxin. Six 7,8‐benzoflavones and eight 5,6‐benzoflavones were synthesized in this study. The NMR data for a few of these compounds have been previously reported; however, the NMR data for most of them have not been reported. For reference purposes, the complete NMR data for the 14 benzoflavones are described. Copyright © 2012 John Wiley & Sons, Ltd.     

Stereochemistry and conformations of natural 1,2-epoxy-guaianolides based on 1D and 2D NMR data and semiempirical calculations

From detailed study of 1D and 2D NMR spectra of ten natural 1,2-epoxyguaianolides (bis-1,2:3,4-epoxyguaianolides and guaianolide-1,2-epoxychlorohydrins), we identified general spectral traits helpful for stereochemical assignment of such sesquiterpene lactones. We found that the chemical shifts of certain (1)H and (13)C nuclei are consistently dependent on the configuration of 1,2-epoxy-ring which could be used as a simple rule for establishing this configuration. Then, from 1D and 2D (COSY, NOESY, HMQC, HMBC) NMR data, applying the observed rule, the structure and stereochemistry of two new, diastereomeric guaianolide-1,2-epoxychlorohydrins, isolated from Achillea serbica, are determined. The NMR data, namely, nuclear overhauser enhancement (NOE) correlations, pointed out two conformations of guaianolide's cycloheptane ring. The semiempirical calculations (AM1 and PM3 methods), performed in order to gain additional information regarding conformations, resulted in three geometries of investigated lactones. Even so, the conformations derived from the NMR data agreed well with those calculated by semiempirical methods.     

Complete 1H NMR spectral analysis of ten chemical markers of Ginkgo biloba

The complete and unambiguous ¹H NMR assignments of ten marker constituents of Ginkgo biloba are described. The comprehensive ¹H NMR profiles (fingerprints) of ginkgolide A, ginkgolide B, ginkgolide C, ginkgolide J, bilobalide, quercetin, kaempferol, isorhamnetin, isoquercetin, and rutin in DMSO‐d₆ were obtained through the examination of 1D ¹H NMR and 2D ¹H,¹H‐COSY data, in combination with ¹H iterative full spin analysis (HiFSA). The computational analysis of discrete spin systems allowed a detailed characterization of all the ¹H NMR signals in terms of chemical shifts (δ_H) and spin‐spin coupling constants (J_HH), regardless of signal overlap and higher order coupling effects. The capability of the HiFSA‐generated ¹H fingerprints to reproduce experimental ¹H NMR spectra at different field strengths was also evaluated. As a result of this analysis, a revised set of ¹H NMR parameters for all ten phytoconstituents was assembled. Furthermore, precise ¹H NMR assignments of the sugar moieties of isoquercetin and rutin are reported for the first time. Copyright © 2012 John Wiley & Sons, Ltd.     

1H and 13C NMR signal assignments of some new spiro[7H-benzo[de]anthracene-naphthopyrans

The complete 1H and 13C NMR signal assignment of four new photochromic spiro[7H-benzo[de]anthracene-naphthopyrans] was achieved using one- and two-dimensional methods (DEPT, COSY, HSQC, HMBC, NOESY).     

Quantitative estimation of the degree of derivatization: an alternative methodology using 1-D and 2-D NMR experiments

The precise estimation of the degree of derivatization of functional groups in polymers is important for determining their macroscopic properties. In this work, the quantitative estimation of the extent of esterification of novolac copolymers with di-tert-butyl dicarbonate was studied. Although the extent of esterification has been calculated previously by quantifying the signals from FT-IR and UV-Vis spectroscopy, these were restricted to monitoring the progress of the derivatization process. The 13C NMR signal intensities from the inverse-gated 1H-decoupled NMR spectrum have been used recently for the quantitative estimation of the degree of esterification of polymers. An alternative methodology has been suggested by us based on the fully relaxed 1H chemical shift intensities. However, since the proton signals of novolac resins are generally broad and overlapping, the proton decoupled 13C NMR spectrum was used to identify the 1H NMR signals using the 2-D HSQC technique. A TOCSY experiment was also performed to confirm further the 1H NMR signal assignments and, finally, the deconvoluted 1H NMR spectrum was used for the calculation of the extent of derivatization.     

NMR对苯并噁嗪类化合物结构的研究

利用'H、'13CNMR谱及HMBC、HMQC二维谱对10种苯并噁嗪类化合物的结构进行了研究,初步得出了它们的NMR谱特征,分析了化学位移的影响因素。     

Complete NMR signal assignments of flavonol derivatives

Common substitution positions of flavonols are at C-5 and C-7; 6-substituted flavonol derivatives are rarely found in natural sources. Here, we report complete assignments of 1H and 13C chemical shifts of eight flavonol derivatives including four 6-substituted flavonols.     

Synthesis and NMR elucidation of novel penta-cycloundecane amine derivatives as potential antituberculosis agents

The synthesis and NMR elucidation of five novel penta-cycloundecane amine derivatives are reported. These compounds are potential antituberculosis agents. The (1)H and (13)C spectra showed major overlapping of methine signals of the cage skeleton making it extremely difficult to elucidate these compounds. The overlapping occurs as a result of the additions made to the carbonyl carbon (C-8/C-11) of the cage. The two-dimensional NMR technique proved to be a useful tool in overcoming this problem. All compounds reported are meso compounds thereby not only simplifying the NMR structure elucidation, but also making it indeed possible.     

Regioselective synthesis and structural elucidation of 1,4-disubstituted 1,2,3-triazole derivatives using 1D and 2D NMR spectral techniques

Regioselective synthesis of 2-[1-(2-oxo-2-phenylethyl)-1H-[1,2,3]triazol-4-ylmethoxy]-benzaldehyde derivatives was achieved by [3 + 2] cycloaddition reaction of 2-(prop)-2-ynyloxy-benzaldehyde derivatives with phenacyl azide. The regiochemistry and the spectral assignments of the synthesized triazole derivatives were studied using both 1D and 2D NMR spectral techniques in solution.     

Complete 1H and 13C NMR assignments of the epimeric menthane-1-carboxylic acids

Complete NMR analyses with full assignments for (1)H and (13)C NMR spectral data for both epimers of menthane-1-carboxylic acid are described. The NMR properties of the recently synthesized axial isomer had not been previously described, and through use of a variety of 1D and 2D techniques, additional information is provided for the equatorial isomer. As well as assignments of chemical shifts, homonuclear coupling constants were determined for the equatorial isomer and most of coupling constants were measured for the axial isomer.     

1H and 13C NMR studies of 2-functionalized 5-(methylsulfonyl)-1-phenyl-1H-indoles

The 1H and 13C NMR resonances of thirty 2-functionalized 5-(methylsulfonyl)-1-phenyl-1H-indoles were assigned completely and unequivocally using the concerted application of one- and two-dimensional experiments (DEPT, gs-HMQC and gs-HMBC). Finally, the influence of the 2-substituent of 5-(methylsufonyl)-1-phenyl-1H-indoles on the carbon atoms of the indole moiety was estimated.     

Synthesis and NMR spectral assignments of novel nitrogen and sulfur heterocyclic compounds

Synthesis and NMR spectral studies of multidentate N and S heterocycles, 1,3,5-tris(N-methylbenzimidazolyl)benzene, 1,3,5-tris(benzimidazolyl)benzene,1,3,5-tris(benzothiazolyl) benzene, 2,2'-bipyridine 3,3'-bis(benzothiazolyl)benzene and 1,2,4,5-tetrakis(benzothiazolyl) benzene have been carried out. 2D (1)H-(1)H PFG-COSY as well as (1)H-(13)C single and multiple bond correlated (2D GRASP-HSQC and GRASP-HMBC) experiments have been employed to characterize the compounds. 1D NOE experiments have been useful in understanding the structure of 1,3,5-tris(N-methylenzimidazolyl)benzene.     

1H and 13C NMR assignments for two new angular furanocoumarin glycosides from Peucedanum praeruptorum

Two novel angular-type furanocoumarin glycosides, peucedanoside A (1) and peucedanoside B (2), along with a known compound apterin (3), were isolated from the roots of Peucedanum praeruptorum Dunn. Their chemical structures were determined by MS, NMR spectroscopy and chemical analysis. Complete assignments of the 1H and 13C NMR spectroscopic data were achieved by 1D and 2D NMR experiments including DEPT, HSQC, HMBC and ROESY.     

Detailed assignments of 1H and 13C NMR spectral data of 14 cyclopentane derivatives

Detailed assignments of ¹H and ¹³C NMR spectral data for 14 cyclopentane derivatives are reported. The assignments are based on 1D ¹H and ¹³C NMR and on 2D shift‐correlated [¹H, ¹³C‐HMQC], J‐resolved and NOEDIF experiments. Copyright © 2003 John Wiley & Sons, Ltd.