R2PI Study of intermolecular hydrogen bond in solvent-free chiral complexes.

Abstract:

:One- and two-color, mass selected R2PI spectra of the S(1)<--S(0) transitions in the bare (+)-(R)-1-phenyl-1-ethanol (E(R)) and its complexes with different solvent molecules (solv) (-)-(R)-2-butanol (B(R)) or (+)-(S)-2-butanol (B(S)) and (-)-(R)-2-butylamine (A(R)) or (+)-(S)-2-butylamine (A(S)), have been recorded after a supersonic molecular beam expansion. The one-color R2PI excitation spectra of the diastereomeric complexes are characterized by significant shifts of their band origin relative to that of bare E(R). The extent and the direction of these spectral shifts are found to depend on the structure and the configuration of solv and are attributed to different short-range interactions in the ground and excited states of the complexes. In analogy with other diastereomeric complexes, the phenomenological binding energy of the homochiral cluster is found to be greater than that of the heterochiral one.

journal_name

Chirality

journal_title

Chirality

authors

Giardini Guidoni A,Piccirillo S,Scuderi D,Satta M,Di Palma TM,Speranza M,Filippi A,Paladini A

doi

10.1002/chir.10010

subject

Has Abstract

pub_date

2001-01-01 00:00:00

pages

727-30

issue

10

eissn

0899-0042

issn

1520-636X

pii

10.1002/chir.10010

journal_volume

13

pub_type

杂志文章
  • Enantioselectivity in the steady-state pharmacokinetics and transplacental distribution of pindolol at delivery in pregnancy-induced hypertension.

    abstract::Nine patients taking oral doses of 10 mg/12 h rac-pindolol as part of their treatment for hypertension in pregnancy were recruited for the study. Maternal and fetal gestational age ranged from 20-38 years and 28-41 weeks, respectively. Blood was collected from the umbilical cord vein and from the mother from zero to 1...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.10124

    authors: Gonçalves PV,Matthes Ado C,Da Cunha SP,Lanchote VL

    更新日期:2002-08-01 00:00:00

  • Separation and determination of tetracycline hydrochloride in real water samples using binary small molecule alcohol-salt aqueous two-phase system coupled with high-performance liquid chromatography.

    abstract::An environmental and sensitive sample pretreatment method was established and combined with high-performance liquid chromatography (HPLC) for the analysis of tetracycline hydrochloride (TC) in feed water and lake water. One element small molecule alcohol-salt aqueous two-phase system (ATPS) cannot effectively adjust t...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.23080

    authors: Guo DG,Ni L,Wang L,Shao L

    更新日期:2019-09-01 00:00:00

  • Heparin-induced circular dichroism of an achiral, bicyclic species.

    abstract::Antimalarial drugs have shown potential in suppressing the role of glycosaminoglycans (GAGs) in the pathology of prion protein conformational disorders (e.g. "Mad Cow" disease) by competing for sites of electrostatic interaction. In this study, circular dichroism (CD) and UV/Visible (UV/Vis) absorption spectroscopy te...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.20873

    authors: Stanley FE,Warner AM,McWilliams KM,Stalcup AM

    更新日期:2011-01-01 00:00:00

  • Highly enantioselective asymmetric autocatalysis of 2-alkenyl- and 2-vinyl-5-pyrimidyl alkanols with significant amplification of enantiomeric excess.

    abstract::2-Alkenyl- and 2-vinyl-5-pyrimidyl alkanols are highly enantioselective asymmetric autocatalysts with significant amplification of enantiomeric excess in the enantioselective addition of diisopropylzinc to 2-alkenyl- and 2-vinylpyrimidine-5-carbaldehydes. Consecutive asymmetric autocatalysis starting from 7% ee increa...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.10068

    authors: Sato I,Yanagi T,Soai K

    更新日期:2002-02-01 00:00:00

  • Polymer-Supported Optically Active fac(S)-Tris(thiotato)rhodium(III) Complex for Sulfur-Bridging Reaction With Precious Metal Ions.

    abstract::The optically active mixed-ligand fac(S)-tris(thiolato)rhodium(III) complexes, ΔL -fac(S)-[Rh(aet)2 (L-cys-N,S)](-) (aet = 2-aminoethanethiolate, L-cys = L-cysteinate) () and ΔLL -fac(S)-[Rh(aet)(L-cys-N,S)2 ](2-) were newly prepared by the equatorial preference of the carboxyl group in the coordinated L-cys ligand. T...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.22546

    authors: Aizawa S,Tsubosaka S

    更新日期:2016-01-01 00:00:00

  • A new water soluble Zn-salophen derivative as a receptor for alpha-aminoacids: unexpected chiral discrimination.

    abstract::A new water soluble zinc-salophen complex with appended D-glucose moieties was synthesized and characterized. Its binding properties toward six aminoacids were investigated by UV-vis spectrophotometric titrations. Association constants showed to be unfavorably affected by increasing steric hindrance of the side chain....

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.20614

    authors: Dalla Cort A,De Bernardin P,Schiaffino L

    更新日期:2009-01-01 00:00:00

  • Chiral investigation of midodrine, a long-acting alpha-adrenergic stimulating agent.

    abstract::Midodrine hydrochloride is a peripheral alpha(1)-adrenoreceptor agonist that induces venous and arterial vasoconstriction. Midodrine, after oral or intravenous administration, undergoes enzymatic hydrolysis and releases deglymidodrine, a pharmacologically active metabolite. Midodrine and deglymidodrine have a chiral c...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.20041

    authors: Quaglia MG,Farina A,Palmery M,Desideri N,Donati E,Bossù E,Strano S

    更新日期:2004-07-01 00:00:00

  • The biological activities of prothioconazole enantiomers and their toxicity assessment on aquatic organisms.

    abstract::Chiral fungicide prothioconazole has a wide range of antifungal spectrum; however, little research has been conducted to evaluate prothioconazole on an enantiomeric level. Five target pathogens and three common aquatic organisms were tested for the enantioselective bioactivity and toxicity of prothioconazole in this w...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.23075

    authors: Zhai W,Zhang L,Cui J,Wei Y,Wang P,Liu D,Zhou Z

    更新日期:2019-06-01 00:00:00

  • Isolation and identification of sapotexanthin 5,6-epoxide and 5,8-epoxide from red mamey (Pouteria sapota).

    abstract::Two new carotenoids, sapotexanthin 5,6-epoxide and sapotexanthin 5,8-epoxide, have been isolated from the ripe fruits of red mamey (Pouteria sapota). Sapotexanthin 5,6-epoxide was also prepared by partial synthesis via epoxidation of sapotexanthin, and the (5R,6S) and (5S,6R) stereoisomers were identified by high-perf...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.23206

    authors: Murillo E,Agócs A,Nagy V,Király SB,Kurtán T,Toribio EM,Lakey-Beitia J,Deli J

    更新日期:2020-05-01 00:00:00

  • Alpha-aminophosphonates as novel organocatalysts for asymmetric Michael addition of carbonyl compounds to nitroolefins.

    abstract::A cyclic alpha-aminophosphonate was found to be a novel organocatalyst for Michael type addition reactions of carbonyl compounds to nitroolefins to afford the corresponding adducts in high enantio- and diastereoselectivities. ...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.20552

    authors: Tao Q,Tang G,Lin K,Zhao YF

    更新日期:2008-07-01 00:00:00

  • Conformational and Chiral Properties of Cyclic-tri(N-methyl-meta-benzamide) Bearing Amidino Groups.

    abstract::Cyclic triamides bearing amidino groups at the meta position of the phenyl rings were synthesized, and their conformational properties in the crystal and in solution were examined. Compound exists as a capsule-type dimer of the enantiomers with a bowl-shaped syn conformation in the crystal state. Compound exists mainl...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.22476

    authors: Nishiyama S,Urushibara K,Masu H,Azumaya I,Kagechika H,Tanatani A

    更新日期:2015-08-01 00:00:00

  • Optically active α-phenylethylamine as efficient organocatalyst in the solvent-free reactions between 2,3-butanedione and conjugated nitroolefins.

    abstract::(R)-(+) and (S)-(-)-1-phenylethylamine have been shown to promote highly diastereoselective and complementary enantioselective formal [3 + 2]carbocyclization reactions between 2,3-butanedione and conjugated nitroalkenes with formation of enantiomerically rich 2-hydroxy-3-nitrocyclopentanone derivatives. The reactions ...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.22088

    authors: Felluga F,Forzato C,Nitti P,Pitacco G,Prati F,Valentin E,Zangrando E

    更新日期:2012-12-01 00:00:00

  • Circular dichroism eigenspectra of polyproline II and β-strand conformers of trialanine in water: Singular value decomposition analysis.

    abstract::Despite that a number of experimental and theoretical investigations have been carried out to determine the structure of trialanine in water, the reported populations of polyproline II (PPII) and β-strand conformers vary and were found to be dependent on which spectroscopic method was used. Such discrepancies are due ...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.20870

    authors: Oh KI,Lee KK,Park EK,Yoo DG,Hwang GS,Cho M

    更新日期:2010-01-01 00:00:00

  • Time-resolved circularly polarized luminescence of Eu3+ -based systems.

    abstract::Chiral Eu3+ -based systems are frequently studied via circularly polarized luminescence spectroscopy. The emission lifetimes of each circular polarization, however, are virtually always ignored, because in a homogeneous sample of emitters, there should be no difference between the two. However, we show that in less ro...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.23293

    authors: Hananel U,Schwartz G,Paiss G,Arrico L,Zinna F,Di Bari L,Cheshnovsky O,Markovich G

    更新日期:2020-12-30 00:00:00

  • Stereoselective kinetics of warfarin binding to human serum albumin: effect of an allosteric interaction.

    abstract::Kinetic and equilibrium binding studies were performed on the interaction of warfarin enantiomers with human serum albumin (HSA) in the absence and presence of lorazepam acetate (LoAc) enantiomers. Binding kinetics were followed by recording changes in the fluorescence of warfarin upon binding to HSA using the stopped...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.10113

    authors: Fitos I,Visy J,Kardos J

    更新日期:2002-05-15 00:00:00

  • Enantioselectivity in the metabolism of mexiletine by conjugation in female patients with the arrhythmic form of chronic Chagas' heart disease.

    abstract::The phenomenon of enantioselectivity in the metabolism of mexiletine (MEX) conjugation was investigated in eight female patients with the arrhythmic form of chronic Chagas' heart disease treated with racemic mexiletine hydrochloride (two 100 mg capsules every 8 hr). Blood samples were collected up to 24 hr after the a...

    journal_title:Chirality

    pub_type: 临床试验,杂志文章

    doi:10.1002/(SICI)1520-636X(1999)11:1<29::AID-CHIR5>3.

    authors: Lanchote VL,Cesarino EJ,Santos VJ,Mere Júnior Y,Santos SR

    更新日期:1999-01-01 00:00:00

  • Enantioselective determination of isradipine in human serum using chiral stationary phase liquid chromatography and gas chromatography with nitrogen selective detection.

    abstract::rac-Isradipine is a dihydropyridine type calcium antagonist. Its calcium entry blocking effect is due primarily to the (+)-(S)-enantiomer. This study describes a sensitive enantioselective method for the determination of isradipine in human serum. Following alkaline extraction into hexane, the enantiomers of isradipin...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/(SICI)1520-636X(1998)10:9<808::AID-CHIR6>3

    authors: Rask HS,Angelo HR,Christensen HR

    更新日期:1998-01-01 00:00:00

  • Optical resolution of 6-fluoro-2-methyl-1,2,3,4-tetrahydroquinoline by supercritical fluid extraction.

    abstract::6-Fluoro-2-methyl-1,2,3,4-tetrahydroquinoline (FTHQ) enantiomers were separated by supercritical fluid extraction using carbon dioxide. Diastereoisomeric salts were formed from the racemic base with less than one equivalent of O,O'-di-(4-toluoyl)-(2R,3R)-tartaric acid (DPTTA). Further purification was achieved by part...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.1178

    authors: Kmecz I,Simándi B,Bálint J,Székely E,Fogassy E,Kemény S

    更新日期:2001-01-01 00:00:00

  • Online sample concentration in partial-filling chiral electrokinetic chromatography – mass spectrometry.

    abstract::The concentration sensitivity of a racemic drug (chlorpheniramine maleate) in chiral capillary electrophoresis with electrospray ionization – mass spectrometric detection was improved ~500-fold via stacking. Enantiomeric separation was achieved through the use of a neutral chiral pseudostationary phase (2-hydroxpropyl...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.22257

    authors: Wuethrich A,Haddad PR,Quirino JP

    更新日期:2014-11-01 00:00:00

  • Chemoenzymatic approach to optically active 4-hydroxy-5-alkylcyclopent-2-en-1-one derivatives: an application of a combined circular dichroism spectroscopy and DFT calculations to assignment of absolute configuration.

    abstract::A series of representative optically active derivatives of 4-hydroxy-5-alkylcyclopent-2-en-1-one were prepared from the respective 2-furyl methyl carbinols via the Piancatelli rearrangement followed by the enzymatic kinetic resolution of racemates. Applicability of chiroptical methods (experimental and calculated elec...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.22322

    authors: Frelek J,Karchier M,Madej D,Michalak K,Różański P,Wicha J

    更新日期:2014-06-01 00:00:00

  • Species differences in the generation of the chiral sulfoxide metabolite of albendazole in sheep and rats.

    abstract::The prochiral anthelmintic drug albendazole was administered orally to sheep and rats. Blood samples were taken at standardized intervals during the time course of the plasma kinetics: 18 h in rats and 48 h in sheep. The enantiomeric ratio of the sulfoxide metabolite was determined by means of HPLC on a chiral station...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.530020306

    authors: Delatour P,Benoit E,Caude M,Tambute A

    更新日期:1990-01-01 00:00:00

  • Separation and quantitation of (R)- and (S)-atenolol in human plasma and urine using an alpha 1-AGP column.

    abstract::A method for the determination of (R)- and (S)-atenolol in human plasma and urine is described. The enantiomers of atenolol are extracted into dichloromethane containing 3% heptafluorobutanol followed by acetylation with acetic anhydride at 60 degrees C for 2 h. The acetylated enantiomers were separated on a chiral al...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.530010306

    authors: Enquist M,Hermansson J

    更新日期:1989-01-01 00:00:00

  • Chiral separation and CD characterisation of enantiomeric cyclotriphosphazene derivatives.

    abstract::The gem-disubstituted cyclotriphosphazene 1 reacted with piperazine (pip) to give the piperazine-bridged derivative 2, which is expected to exist in meso and racemic forms because the two PCl (pip) groups are stereogenic. The proton-decoupled (31)P NMR spectrum of 2 gave rise to two similar sets of ABX signals in a 1:...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.20187

    authors: Bui TT,Coles SJ,Davies DB,Drake AF,Eaton RJ,Hursthouse MB,Kiliç A,Shaw RA,Yeşilot S

    更新日期:2005-10-01 00:00:00

  • Short step enantioselective synthesis of (-)-swainsonine.

    abstract::Recent discovery of asymmetric desymmetrization of meso-heterocycles using (R,R)-(salen)manganese complex 2 as a catalyst allowed easy access to optically active 2,3,4-trisubstituted pyrrolidines. Taking advantage of this new reaction, we could achieve the short-step synthesis of (-)-swainsonine 1. ...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/(SICI)1520-636X(2000)12:5/6<464::AID-CHIR2

    authors: Punniyamurthy T,Irie R,Katsuki T

    更新日期:2000-06-01 00:00:00

  • Unprecedented crystallization and X-ray crystal structure of racemic N(alpha)-(t-butyloxycarbonyl)-L-L-phenylalanine N-methoxy-N-methylamide.

    abstract::Weinreb amide 3 was synthesized using isobutyl chloroformate, carbonyldiimidazole, or ethylcarbodiimide as the coupling agent in the reaction of Boc-phenylalanine with O,N-dimethylhydroxylamine hydrochloride. An optically active oil was isolated along with an optically inactive solid irrespective of the type of coupli...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/(SICI)1520-636X(2000)12:1<2::AID-CHIR2>3.0

    authors: Zheng X,Donkor IO,Miller DD,Ross CR 2nd

    更新日期:2000-01-01 00:00:00

  • An integrating sphere to measure CD from difficult samples

    abstract::Integrating spheres are widely used with UV-Vis and occasionally with infrared spectrophotometers to measure different types of samples, either in transmission mode (scattered transmission accessories) or in total/diffuse reflectance mode. We built a prototype sphere of the demountable type, which fits easily the samp...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/(SICI)1520-636X(2000)12:4<291::AID-CHIR16>

    authors: Castiglioni E,Albertini P

    更新日期:2000-05-01 00:00:00

  • Chiral discrimination of the analgesic cizolirtine by using cyclodextrins: A (1)H NMR study on the solution structures of their host-guest complexes.

    abstract::The use of four cyclodextrins (three native and one beta-CD derivative) as NMR chiral solvating agents to resolve the enantiomers of (+/-)-cizolirtine, 1, and its chemical precursor (the carbinol, (+/-)-2), was investigated. The best enantiodiscrimination occurred when beta-cyclodextrin was used. ROESY experiments wer...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/(SICI)1520-636X(1999)11:9<694::AID-CHIR5>3

    authors: Redondo J,Blázquez MA,Torrens A

    更新日期:1999-01-01 00:00:00

  • N,N-dimethylcarbamyl derivatives of oxazepam.

    abstract::Three N,N-dimethylcarbamyl derivatives of oxazepam (1-(N,N-dimethylcarbamyl)oxazepam, 3-O-(N,N-dimethylcarbamyl)oxazepam, and 1,3-O-bis(N,N-dimethylcarbamyl) oxazepam) and a 3-O-acyl-1-(N,N-dimethylcarbamyl)-oxazepam were synthesized from either oxazepam or demoxepam. Enantiomeric pairs of these derivatives and of cam...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.530030313

    authors: Yang SK,Lu XL

    更新日期:1991-01-01 00:00:00

  • Novel P,N-bidentate phosphite ligands in asymmetric catalysis.

    abstract::Results achieved by the authors in the synthesis of chiral P,N-phosphite ligands are summarized. Three groups of new chiral P,N-phosphites are discussed, namely, ligands derived from 1,1'-bi-2-naphthol, ligands possessing an acyclic phosphorus center, and P*-chiral ligands derived from (S)-2-anilinomethylpyrrolidine. ...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.10258

    authors: Gavrilov KN,Bondarev OG,Korostylev AV,Polosukhin AI,Tsarev VN,Kadilnikov NE,Lyubimov SE,Shiryaev AA,Zheglov SV,Gais HJ,Davankov VA

    更新日期:2003-01-01 00:00:00

  • Computational simulation of vibrationally resolved spectra for spin-forbidden transitions.

    abstract::In this computational study, we illustrate a method for computing phosphorescence and circularly polarized phosphorescence spectra of molecular systems, which takes into account vibronic effects including both Franck-Condon and Herzberg-Teller contributions. The singlet and triplet states involved in the phosphorescen...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.22864

    authors: Egidi F,Fusè M,Baiardi A,Bloino J,Li X,Barone V

    更新日期:2018-07-01 00:00:00