Solid-State Structures and Solution Analyses of a Phenylpropylpyridine N-Oxide and an N-Methyl Phenylpropylpyridine

被引：20

作者：

Richter, Isabella ^{[1
]}

Warren, Mark R. ^{[1
]}

Minari, Jusaku

Elfeky, Souad A. ^{[1
]}

Chen, Wenbo ^{[1
]}

Mahon, Mary E. ^{[1
]}

Raithby, Paul R. ^{[1
]}

James, Tony D. ^{[1
]}

Sakurai, Kazuo

Teat, Simon J. ^{[2
]}

Bull, Steven D. ^{[1
]}

Fossey, John S. ^{[1
]}

机构：

[1] Univ Bath, Dept Chem, Bath BA2 7AY, Avon, England

[2] Univ Calif Berkeley, Lawrence Berkeley Lab, Adv Light Source, Berkeley, CA 94720 USA

来源：

CHEMISTRY-AN ASIAN JOURNAL | 2009年 / 4卷 / 01期

基金：

英国工程与自然科学研究理事会;

关键词：

cations; fluorescence; hydrogen bonds; alkylpyridines; pi-stacking; LEONARD LINKER COMPOUNDS; PI-STACKING INTERACTIONS; AROMATIC INTERACTIONS; CRYSTALLOGRAPHIC EVIDENCE; INTRAMOLECULAR CATION; ARENE INTERACTIONS; CONFORMATION; RECOGNITION; PROTEINS; KINETICS;

D O I：

10.1002/asia.200800255

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The crystal structures of phenylpropylpyridine-N-oxide and N-methyl-phenylpropylpyridinium iodide are compared, revealing that hydrogen bonding with the solvent molecule plays an important role in the N-oxide compound, whilst electrostatic interactions are predominant in controlling the solid-state orientation of the N-methylated compound. Fluorescence spectroscopy and NOESY indicate that in contrast to the previously reported pyridinium iodide, the N-oxide is not subject to intramolecular pi-stacking, as judged by excimer emission and a lack of corresponding cross peaks, respectively.

引用

页码：194 / 198

页数：5

共 50 条

[31] LUMINESCENCE OF POLY(N-VINYLCARBAZOLE) IN SOLUTION AND SOLID-STATE
JEZEK, B
POSPISIL, J
CHUDACEK, I
NARKEVICHIUS, V
VAITKUS, J
CZECHOSLOVAK JOURNAL OF PHYSICS, 1975, 25 (10) : 1176 - 1180
[32] Solution and solid-state conformational and structural analysis of the N-methyl derivatives of (±)-threo-methylphenidate, (±)-erythro-methylphenidate, and (±)-threo-p-methyl-methylphenidate hydrochloride salts
Glaser, R
Adin, I
Shiftan, D
Shi, Q
Deutsch, HM
George, C
Wu, KM
Froimowitz, M
JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (06): : 1785 - 1794
[33] STRUCTURE AND PROPERTIES OF CELLULOSE AND CELLULOSE GUAR BLEND MEMBRANES PREPARED FROM THE N-METHYL MORPHOLINE N-OXIDE WATER SOLVENT SYSTEM
LUO, M
WINTER, WT
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1995, 209 : 5 - CELL
[34] STUDY OF ORDERED STRUCTURES OF SYNDIOTACTIC POLY(METHYL METHACRYLATE) IN SOLUTION AND IN THE SOLID-STATE
SPEVACEK, J
SCHNEIDER, B
DYBAL, J
STOKR, J
BALDRIAN, J
JOURNAL OF POLYMER SCIENCE PART B-POLYMER PHYSICS, 1984, 22 (04) : 617 - 635
[35] Excited-State Forms of 2-Methylamino-6-methyl-4-nitropyridine N-Oxide and 2-Butylamino-6-methyl-4-nitropyridine N-Oxide
Makarewicz, Artur
Szemik-Hojniak, Anna
van der Zwan, Gert
Deperasinska, Irena
JOURNAL OF PHYSICAL CHEMISTRY A, 2009, 113 (15): : 3438 - 3446
[36] Solid-state characterization of an NR2B selective N-methyl D-aspartate (NMDA) antagonist polymorphs
Kojima, Takashi
Sato, Morimichi
Omura, Atsushi
Kawai, Makoto
Sakai, Mio
Matsuoka, Yoko
Murata, Yoshinori
Hattori, Kazunari
Sakemi, Shinichi
Bordner, Jon
Samardjiev, Ivan
Mano, Takashi
INTERNATIONAL JOURNAL OF PHARMACEUTICS, 2008, 355 (1-2) : 337 - 340
[37] CELLULOSE ORGANIC-SOLVENTS .1. THE STRUCTURES OF ANHYDROUS N-METHYLMORPHOLINE N-OXIDE AND N-METHYLMORPHOLINE N-OXIDE MONOHYDRATE
MAIA, E
PEGUY, A
PEREZ, S
ACTA CRYSTALLOGRAPHICA SECTION B-STRUCTURAL SCIENCE, 1981, 37 (OCT): : 1858 - 1862
[38] CU(II) COMPLEXES OF N-METHYL-2-PICOLINAMINE N-OXIDE
WEST, DX
HARTLEY, RJ
JOURNAL OF INORGANIC & NUCLEAR CHEMISTRY, 1980, 42 (08): : 1141 - 1144
[39] ELECTROCHEMISTRY OF ALLOXAN AND ITS N-METHYL DERIVATIVES IN AQUEOUS SOLUTION
HANSEN, BH
DRYHURST, G
JOURNAL OF THE ELECTROCHEMICAL SOCIETY, 1971, 118 (11) : 1747 - &
[40] SOLID-STATE STRUCTURE OF N,N-DIBENZYLHYDROXYLAMINE
MITZEL, NW
RIEDE, J
ANGERMAIER, K
SCHMIDBAUR, H
ZEITSCHRIFT FUR NATURFORSCHUNG SECTION B-A JOURNAL OF CHEMICAL SCIENCES, 1995, 50 (04): : 699 - 701

← 1 2 3 4 5 →