15N‐ und 13 C‐NMR‐chemische Verschiebungen sowie 13C‐1H‐, 13C‐15N‐ und 15N‐15N‐Spin‐Spin‐Kopplungskonstanten para‐substituierter Benzendiazoniumsalze

Грүнер, Маргит; Pfeifer, Dietmar; Becker, H. G. O.; Radeglia, R.; Epperlein, J.

doi:10.1002/prac.19853270109

Cited by 11 publications

(5 citation statements)

References 38 publications

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“…Here, we targeted an aminobenzyl functionalization instead of a clickable terminal group in order to enable eventual thiourea‐bridging (and also other grafting steps such as peptide coupling). Thus, for fabrication of amino‐prefunctionalized ND 7 , milled36 detonation nanodiamond 4 was coupled with 4‐cyanobenzenediazonium tetrafluoroborate 5 ,34 obtained by diazotization of 4‐aminobenzonitrile in a Sandmeyer reaction as published previously37 (Scheme ). This sequence afforded nanodiamond 6 carrying 4‐cyanophenyl groups.…”

Section: Resultsmentioning

confidence: 99%

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Thiourea‐Bridged Nanodiamond Glycoconjugates as Inhibitors of Bacterial Adhesion

Fessele¹,

Wachtler

Chandrasekaran³

et al. 2015

Eur J Org Chem

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The study of bacterial adhesion is crucial to our understanding of infection processes as well as for the development of antiadhesives. Here we have investigated new nanodiamond glycoconjugates intended to inhibit adhesion of type 1 fimbriated E. coli bacteria. For conjugation of saccharides and nanodiamond, thiourea‐bridging was employed, a method that has not been used before in nanodiamond derivatization. Amino‐prefunctionalized diamond nanoparticles were prepared employing aromatic diazonium salts and reacted with different isothiocyanato‐functionalized mannose derivatives. The resulting glyconanodiamonds were characterized and then tested in bacterial binding assays. They are recognized by the bacterial protein FimH according to the structure‐activity relationships known for this lectin. Thus, owing to the particular properties of nanodiamond, a valuable material is introduced with the potential to control bacterial adhesion and colonization in a favorable way.

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Section: Resultsmentioning

confidence: 99%

“…Synthesis of Mannose Derivatives: The isothiocyanato‐functionalized mannose derivatives 1 ,35 2 ,36 and 3 ,37 that were employed for GND preparation, were synthesized according to the literature. The measured analytical data were in full accordance with the literature.…”

Section: Methodsmentioning

confidence: 99%

Thiourea‐Bridged Nanodiamond Glycoconjugates as Inhibitors of Bacterial Adhesion

Fessele¹,

Wachtler

Chandrasekaran³

et al. 2015

Eur J Org Chem

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“…Other substituents that show similar enhanced effects are SeCH=sH2 ( b = 1.537, pg/p," = 1.41,5 I (b=1.475)5 and N=N-(b=1.66). 16 All the carbons of the unsubstituted ring of series 1 compounds gave reasonably good Lynch plots (Table 7), and the negative value for b at C-1' is reflected in the reverse DSP correlations below (b = -0.56, p E / p z = -0.53).…”

Section: Correlations With Benzene Substituent Chemical Shifts (Lynchmentioning

confidence: 88%

NMR study of substituent effects in 4‐substituted and 4,4′‐disubstituted diphenyl sulphides

Chandrasekaran

Perumal

Wilson³

1987

Magnetic Reson in Chemistry

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The proton and carbon NMR spectra of nine 4-X-diphenyl sulphides (series l), seven 4-X-4'-N02-diphenyl sulphides (series 2) and eight 4,4'-X2-diphenyl sulphides (series 3) have been obtained. Correlation of the I3C chemical shifts with the appropriate substituent chemical shifts (SCS) for monosubstituted benzenes (Lynch plots) show an enhancement of substituent effect at C-1 (carbon para to the substituent) in series 1 and 2, but not in series 3. The carbons of the unsubstituted ring in series 1 also correlate with C,-SCS, with slopes of less than unity; correlation for C-1' has a negative slope. Dual substituent parameter (DSP) correlations of the 13C chemical shifts with u,/u$ are good to excellent for all the carbons of series 1 compounds, except those ortho to the substituent X. The carbons meta to the substituent X correlate well, but with negative values for pI and pR, although showing a scattered Lynch plot. Similar correlations are found with some carbon shifts in series 2, and with C-1 shifts in series 3.It is concluded that (a) reverse resonance effects are operative at the position meta to the variable substituent by virtue of the sulphur substituent ortho to that carbon; (b) there is transmission of inductive (field) and resonance effects from one aryl ring to the other, except when both rings carry substituents of the same electronic character (series 3); (c) there is some evidence for m-polarization in the unsubstituted phenyl ring of series 1 compounds.

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“…2-Chloromethylacrylic acid ethyl ester ( 2 g ) was prepared according to procedures described in refs d,e: 1 H NMR (CDCl 3 , 250 MHz) δ 1.32 (t, J = 7.1 Hz, 3 H), 4.26 (q, J = 7.1 Hz, 2 H), 4.29 (dd, J = 0.4 Hz, J = 1.2 Hz, 2 H), 5.96 (m, 1H), 6.38 (m, 1 H); 13 C NMR (CDCl 3 , 63 MHz) δ 14.1 (CH 3 ), 42.6 (CH 2 ), 61.2 (CH 2 ), 128.4 (CH 2 ), 137.1 (C q ), 165.0 (C q ); GC-MS (EI) m / z (%) 150 (1) [ 37 Cl − M + ], 148 (4) [ 35 Cl − M + ], 122 (29), 120 (86), 113 (62), 105 (34), 103 (100), 95 (18), 85 (25), 75 (35).…”

Section: Methodsmentioning

confidence: 99%

“…Ethyl ( Z )-3-bromopropenoate ( 2n ) was prepared according to the procedure described in ref f: 1 H NMR (CDCl 3 , 250 MHz) δ 1.31 (t, J = 7.1 Hz, 3 H), 4.23 (q, J = 7.1 Hz, 2 H), 6.60 (d, J = 8.3 Hz, 1 H), 6.98 (d, J = 8.3 Hz, 1 H); 13 C NMR (CDCl 3 , 63 MHz) δ 14.1 (CH 3 ), 60.7 (CH 2 ), 121.1 (CH), 124.5 (CH), 163.9 (C q ); GC-MS (EI) m / z (%) 180 (1) [ 81 Br − M + ], 178 (1) [ 79 Br − M + ], 152 (20), 150 (20), 135 (98), 133 (100), 107 (21), 105 (22), 99 (63).…”

Section: Methodsmentioning

confidence: 99%

Allylation and Vinylation of Aryl Radicals Generated from Diazonium Salts

et al. 2007

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Allylation and vinylation of aryl radicals generated from aryl diazonium salts provides rapid and efficient access to chlorinated and brominated derivatives of styrene and allylbenzene. Allyl chlorides were found to be better substrates than bromides due to decreased halogen transfer. Donor- and acceptor-substituted diazonium salts are well tolerated. The products represent important precursors for numerous further transformations.

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¹⁵N‐ und ¹³ C‐NMR‐chemische Verschiebungen sowie ¹³C‐¹H‐, ¹³C‐¹⁵N‐ und ¹⁵N‐¹⁵N‐Spin‐Spin‐Kopplungskonstanten para‐substituierter Benzendiazoniumsalze

Cited by 11 publications

References 38 publications

Thiourea‐Bridged Nanodiamond Glycoconjugates as Inhibitors of Bacterial Adhesion

Thiourea‐Bridged Nanodiamond Glycoconjugates as Inhibitors of Bacterial Adhesion

NMR study of substituent effects in 4‐substituted and 4,4′‐disubstituted diphenyl sulphides

Allylation and Vinylation of Aryl Radicals Generated from Diazonium Salts

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