Effect of Substituent of Roof Shape Amines on the Molecular Recognition of Optically Active Acids by NMR Spectroscopy

被引：3

作者：

Gupta, Riddhi ^{[1
]}

Gonnade, Rajesh G. ^{[2
]}

Bedekar, Ashutosh V. ^{[1
]}

机构：

[1] Maharaja Sayajirao Univ Baroda, Fac Sci, Dept Chem, Vadodara 390002, India

[2] CSIR Natl Chem Lab, Ctr Mat Characterizat, Dr Homi Bhabha Rd, Pune 411008, Maharashtra, India

来源：

CHEMISTRYSELECT | 2020年 / 5卷 / 42期

关键词：

Chiral Solvating Agents; Molecular Recognition; NMR spectroscopy; Roof Shape Amine; UV spectroscopy; CHIRAL SOLVATING AGENTS; INDICATOR-DISPLACEMENT ASSAYS; RAY CRYSTAL-STRUCTURES; ENANTIOMERIC EXCESS; ABSOLUTE-CONFIGURATION; DERIVATIZING AGENTS; P-31; NMR; ENANTIOSELECTIVE RECOGNITION; INCLUSION-COMPOUNDS; STATIONARY PHASES;

D O I：

10.1002/slct.202003338

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Optically active roof shape derivatives of benzyl amines were synthesized and screened as chiral solvating agents for the study of molecular recognition of chiral compounds by NMR and UV spectroscopy. The effect of substituents on the aromatic ring of benzyl unit is investigated to assess the binding ability with the analyte and an experimental correlation is observed. Altering the substituents on the ring of benzyl amine and the acidic substrates, significantly influence the CSA interactions. The supramolecular interactions between acid and amine in the single crystal X-ray analysis of the diastereomeric salts provide further insight of the mode of molecular recognition.

引用

页码：13183 / 13190

页数：8

共 95 条

[1] Determination of the enantiomeric excess of chiral carboxylic acids by 31P NMR with C2 symmetrical diamines [J].

Alexakis, A ;

Chauvin, AS .

TETRAHEDRON-ASYMMETRY, 2001, 12 (10) :1411-1415

[2] Effects of a series of dihydroanthracene derivatives on drug efflux in multidrug resistant cancer cells [J].

Alibert, S ;

Santelli-Rouvier, C ;

Castaing, M ;

Berthlot, M ;

Spengler, G ;

Molnar, J ;

Barbe, J .

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2003, 38 (03) :253-263

[3] Synthesis and effects on chloroquine susceptibility in Plasmodium falciparum of a series of new dihydroanthracene derivatives [J].

Alibert, S ;

Santelli-Rouvier, C ;

Pradines, B ;

Houdoin, C ;

Parzy, D ;

Karolak-Wojciechowska, J ;

Barbe, J .

JOURNAL OF MEDICINAL CHEMISTRY, 2002, 45 (15) :3195-3209

[4]

ANDERSON RC, 1984, J ORG CHEM, V49, P1304, DOI 10.1021/jo00181a042

[5]

[Anonymous], 2008, DYNAMIC STEREOCHEMIS

[6]

[Anonymous], 2006, CHIRAL ANAL

[7] Fluorinated Boronic Acid-Appended Bipyridinium Salts for Diol Recognition and Discrimination via 19F NMR Barcodes [J].

Axthelm, Joerg ;

Goerls, Helmar ;

Schubert, Ulrich S. ;

Schiller, Alexander .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2015, 137 (49) :15402-15405

[8] (S)-Naproxen® and (S)-Ibuprofen® chlorides -: convenient chemical derivatizing agents for the determination of the enantiomeric excess of hydroxy and aminophosphonates by 31P NMR [J].

Blazewska, K ;

Gajda, T .

TETRAHEDRON-ASYMMETRY, 2002, 13 (07) :671-674

[9]

Cagliero C., 2016, J CHEM, V56, P925, DOI DOI 10.1002/IJCH.201600091

[10] Simple and efficient methods for discrimination of chiral diacids and chiral alpha-methyl amines [J].

Chaudhari, Sachin R. ;

Suryaprakash, N. .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2012, 10 (31) :6410-6419

← 1 2 3 4 5 6 7 8 9 10 →