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1.
He J Polavarapu PL 《Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy》2005,61(7):1327-1334
The enantiomers of 2-(2-chlorophenoxy) propanoic acid and 2-(3-chlorophenoxy) propanoic acid were resolved on a chiral HPLC column and investigated using mid-infrared vibrational circular dichroism (VCD). Experimental infrared vibrational absorption and VCD spectra were measured in CDCl3 solution in the 2000-900 cm-1 region and compared with the ab initio predictions of absorption and VCD spectra. The predicted spectra were obtained with density functional theory using B3LYP/6-31G* basis set for the stable and dominant conformers. But the predicted spectra did not provide unambiguous structural information due to intermolecular hydrogen bonding in solution. To eliminate the hydrogen bonding effects, the acids were converted to the corresponding methyl esters and the experimental absorbance and VCD spectra of methyl esters were measured. B3LYP predicted spectra were also obtained for the stable and dominant conformers of the esters. From a comparison of the experimental VCD spectra of methyl esters with corresponding ab initio predictions, the absolute configurations of esters, and therefore of their parent acids, are unambiguously determined to be (+)-(R). 相似文献
2.
Góbi S Vass E Magyarfalvi G Tarczay G 《Physical chemistry chemical physics : PCCP》2011,13(31):13972-13984
The vibrational circular dichroism (VCD) spectrum of S-(-) and R-(+)-2-chloropropionic acid is thoroughly analyzed. Besides the VCD spectrum of the monomer, the dimers (stabilized by strong hydrogen bonds) and the 2-chloropropionic acid-CHCl(3) complexes (stabilized by a weak hydrogen bond) are studied both experimentally (in solution and in low-temperature Ar matrix) and by quantum chemical computations. It is shown that dimer formation drastically changes, and even weak complex formation can also substantially affect the overall shape of the VCD spectrum. The present and previous results can be generalized for the practice of absolute configuration determination of carboxylic acids by VCD spectroscopy. For these measurements, if bulky groups do not block dimer formation, comparison of the computed spectra of the dimers with the experimental spectra recorded in relatively concentrated (~0.1 mol dm(-3)) solutions is suggested. Our study also shows that due to the stabilization of monomers and/or the formation of weak complexes, the VCD spectrum recorded in CHCl(3) is more complex and, like in the present case, can have a lower intensity than that of the spectrum recorded in CCl(4). Therefore, if solubility allows, CCl(4) is a much preferred solvent over CHCl(3). 相似文献
3.
Evidence of Dihydrogen Bonding of a Chiral Amine–Borane Complex in Solution by VCD Spectroscopy
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Dr. Christian Merten Christopher J. Berger Dr. Robert McDonald Prof. Dr. Yunjie Xu 《Angewandte Chemie (International ed. in English)》2014,53(37):9940-9943
IR and vibrational circular dichroism (VCD) spectra of a chiral amine–borane in solution are investigated. By comparison of experimental and calculated spectra, unique VCD spectral signatures, which can be attributed to the formation of dihydrogen‐bonded dimers in solution, are identified for the first time. These VCD features are highly sensitive to the specific dihydrogen‐bonding topologies utilized by the chiral amine–borane subunits and thus provide direct structural information of these dihydrogen‐bonded species in solution. Differences in the dihydrogen binding arrangements in solution and in solid state are also revealed. 相似文献
4.
本文通过不同的手性二胺(pn=1,2-丙二胺、chxn=1,2-环己二胺、dpen=1,2-二苯基乙二胺)与脱氢乙酸(dha)缩合,获得了N_2O_2型手性席夫碱配体(dha-en),进而合成了相应的三对手性席夫碱Cu(Ⅱ)络合物([Cu(dha-R/S-pn)](1a和1b)、[Cu(dha-R,R/S,S-chxn)](2a和2b)、[Cu(dha-R,R/S,S-dpen)](3a和3b),对其进行的固体和溶液电子圆二色(ECD)及溶液振动圆二色(VCD)光谱测试表明,这些化合物在固体和溶液状态下的金属中心的主要配位模式和绝对构型基本一致。此外,通过单晶结构分析发现:对于络合物2a/2b以及3a/3b,中心金属Cu(Ⅱ)除了与手性dha-en四齿配位外,还与相邻分子内酯环上的羰基发生弱的轴向配位形成一维超分子螺旋链,即实现了配位键构筑的席夫碱络合物的手性超分子自组装。本文对两对手性络合物2a/2b以及3a/3b的手性结构基元及其与超分子螺旋之间的关系进行了讨论。将本文所获实验VCD光谱数据与文献报道的相关数据进行比对分析,可以相互印证,并呈现一定的绝对构型关联规律且具有手性配位立体化学结构的指纹特征。 相似文献
5.
Lassen PR Guy L Karame I Roisnel T Vanthuyne N Roussel C Cao X Lombardi R Crassous J Freedman TB Nafie LA 《Inorganic chemistry》2006,45(25):10230-10239
The infrared and vibrational circular dichroism (VCD) spectra of six chiral oxorhenium(V) complexes, bearing a hydrotris(1-pyrazolyl)borate (Tp) ligand, have been investigated. These complexes are promising candidates for observation of parity violation (symmetry breaking due to the weak nuclear force). New chiral oxorhenium complexes have been synthesized, namely, [TpReO(eta2-O(CH3)CH2CH2O-O,O)] (4a and 4b) diastereomers and [TpReO(eta2-N(CH3)CH2CH2O-N,O)] (5) and [TpReO(eta2-N(tBu)CH2CH2O-N,O)] (6) enantiomers. All compounds could be obtained in enantiomerically pure form by using either column chromatography or HPLC over chiral columns. VCD spectroscopy of these compounds and of [TpReO(eta2-N(CH3)CH(CH3)CH(Ph)O-N,O)] (2) and [TpReO(eta2-N(CH2)3CHCO2-N,O)] (3) (with chiral bidentate ligands derived, respectively, from ephedrine and proline) were studied. This allowed the absolute configuration determination of all compounds together with their conformational analysis, by comparing calculated and experimental spectra. This is the first VCD study of rhenium complexes which further demonstrates the applicability of VCD spectroscopy in determining the chirality of inorganic complexes. 相似文献
6.
Structural aspects of proton-bound dimers composed of amino acids with aliphatic side chains are investigated using infrared multiple photon dissociation (IRMPD) spectroscopy and electronic structure calculations. Features in the IRMPD spectra in the 700-2,000 cm-1 range are due primarily to C=O stretching, NH2 bending, and COH bending. It was possible to distinguish between isomeric structures by comparing the experimental IRMPD spectra and those predicted using B3LYP/6-31+G(d,p). It was possible, based on the calculations and IRMPD spectra, to assign the experimental spectrum of the glycine proton-bound dimer to a structure which was slightly different from that assigned by previous spectroscopic investigations and in agreement with recent thermochemical studies. Since all proton-bound dimers studied here, composed of the different amino acids, have very similar spectra, it is expected that they also have very similar lowest-energy structures including the mixed alanine/glycine proton-bound dimer. In fact, the spectra are so similar that it would be very challenging to distinguish, for example, the glycine proton-bound dimer from the alanine or valine proton-bound dimers in the 700-2,000 cm-1 range. According to the calculated IR spectra it is shown that in the approximately 2,000-3,200 cm-1 range differentiating between different structures as well as different proton-bound dimers may be possible. This is due mainly to differences in the asymmetric stretch of the binding proton which is predicted to occur in this region. 相似文献
7.
Aamouche A Devlin FJ Stephens PJ Drabowicz J Bujnicki B Mikołajczyk M 《Chemistry (Weinheim an der Bergstrasse, Germany)》2000,6(24):4479-4486
Mid-infrared vibrational unpolarised absorption and vibrational circular dichroism (VCD) spectra of CCl4 solutions of tert-butyl methyl sulfoxide (1) are reported. The spectra are compared to ab initio density functional theory (DFT) calculations carried out using two functionals, B3PW91 and B3LYP, and two basis sets, 6-31G* and TZ2P. The VCD spectra are calculated using Gauge-invariant atomic orbitals (GIAOs). The analysis of the VCD spectrum confirms the R(-)/S(+) absolute configuration of 1. The advantages and disadvantages of VCD spectroscopy in determining the absolute configurations of chiral sulfoxides are discussed. 相似文献
8.
TeresaB. Freedman Xiaolin Cao LaurenceA. Nafie Monica Kalbermatter Anthony Linden AndreasJohannes Rippert 《Helvetica chimica acta》2003,86(9):3141-3155
Biphenyls with only two substituents at the ‘peri'‐position normally show rotation about their chiral axis at room temperature. Using vibrational circular dichroism (VCD), we found no evidence for rotation of (P)‐2′‐[(4S)‐4,5‐dihydro‐4‐(1‐methylethyl)oxazol‐2‐yl][1,1′‐biphenyl]‐2‐methanol ((P,S)‐ 1 ) in CDCl3 about its chiral axis due to stabilization by intramolecular H‐bonding. All rotamers of 1 were calculated at the DFT level, and, from these optimized structures, the VCD spectra were calculated and compared to the measured VCD spectra. The best agreement between calculated and measured spectra is obtained when two rotamers are present in solution. These rotamers differ primarily in their intramolecular H‐bonding interactions, having either OH???N (the form present in the solid state) or OH???O H‐bonds, i.e., a rotation of the heterocycle in 1 takes place in solution. 相似文献
9.
Brotin T Cavagnat D Dutasta JP Buffeteau T 《Journal of the American Chemical Society》2006,128(16):5533-5540
Vibrational circular dichroism (VCD) measurements and density functional theory (DFT) calculations were used to obtain the absolute configuration of optically pure cryptophane-A molecule. This large molecule (120 atoms) that possess a globular shape, but no chiral centers, exceeds the molecular size of published structures for which VCD has been used to determine the absolute configuration. VCD spectra recorded in CDCl(3) solution for the two resolved enantiomers are near mirror images, and very good agreement between the observed IR and VCD spectra and intensity calculations performed at the DFT (B3PW91/6-31G) level establish, besides the absolute configuration, the preferential anti conformation of the aliphatic linkers of the chloroform-cryptophane-A complex. Experiments performed in CD(2)Cl(2) and C(2)D(2)Cl(4) solutions show no significant modifications in the IR and VCD spectra, indicating that the conformation of the aliphatic linkers is similar for empty (C(2)D(2)Cl(4) solution) and encaged (CDCl(3) and CD(2)Cl(2) solutions) cryptophane-A molecules. 相似文献
10.
Petrovic AG Polavarapu PL Drabowicz J Zhang Y McConnell OJ Duddeck H 《Chemistry (Weinheim an der Bergstrasse, Germany)》2005,11(14):4257-4262
The enantiomers of 3,3,3',3'-tetramethyl-1,1'-spirobi[3 H,2,1]benzoxaselenole have been separated on a chiral preparative chromatographic column. The experimental vibrational circular dichroism (VCD) spectra have been obtained for both enantiomers in CH(2)Cl(2). The theoretical VCD spectra have been obtained by means of density functional theoretical calculations with the B3 LYP density functional. From a comparison of experimental and theoretical VCD spectra, the absolute configuration of an enantiomer with positive specific rotation in CH(2)Cl(2) at 589 nm is determined to be R. This conclusion has been verified by comparing results of experimental optical rotatory dispersion (ORD) and electronic circular dichroism (ECD) to predictions of the same properties using the B3 LYP functional for the title compound. 相似文献
11.
The infrared vibrational absorption (VA) and vibrational circular dichroism (VCD) spectral features of L-(+)-lactic acid (LA) in CDCl3 solution are concentration dependent, showing evidence of oligomerization with increasing concentrations. To understand the observed spectra, geometry optimizations, vibrational frequencies, and VA and VCD intensities were evaluated for (LA)n with n=1-4 using density functional theory calculations at the B3LYP6-311++G(d,p), B3LYP/cc-pVTZ, and in some cases, B3LYP/aug-cc-pVTZ levels of theory. Comparisons with the experimental spectra indicate that the lowest energy LA dimer (AA), formed by two C Double Bond O...HO hydrogen bonds, is one of the dominating species in solution at room temperature. Possible contributions from the LA trimer and tetramer are also discussed. To model the VA and VCD spectra of LA in water and in methanol, both implicit polarizable continuum model and explicit hydrogen bonding considerations were used. For explicit hydrogen bonding, geometry optimizations of the AA-(water)n and AA-(methanol)n complexes, with n=2,4,6, were performed, and the corresponding VA and VCD spectra were simulated. Comparisons of the calculated and experimental VA and VCD spectra in the range of 1000-1800 cm(-1) show that AA-(water)n with n=6 best reproduces the experimental spectra in water. On the other hand, AA-(methanol)n with n=2 reproduces well the experimental results taken in methanol solution. In addition, we found evidence of chirality transfer, i.e., some vibrational bands of the achiral water subunits gain VCD strength upon complexation with the chiral LA solute. The study is the first to use VCD spectroscopy to probe the structures of LA aggregates and hydrogen bonding solvation clusters in the solution phase. 相似文献
12.
Sadlej J Dobrowolski JC Rode JE Jamróz MH 《The journal of physical chemistry. A》2007,111(42):10703-10711
This paper presents a discussion of the interaction energies for selected conformers of chiral l-cysteine and their (1:1) complexes with water at the B3LYP/aug-cc-pVDZ level. From among more than forty calculated 1:1 complexes three groups of complexes were singled out and examined by the B3LYP/aug-cc-pVDZ calculated vibrational circular dichroism (VCD) spectra. On the basis of analysis of the nu(OmicronEta) and nu(NuEta) and beta(OH2) and beta(NH2) ranges, the VCD spectra were found to be sensitive to conformational changes and water arrangement in cysteine complexes, and to be especially useful for discriminating between different chiral forms of intermolecular hydrogen-bonding complexes. In particular, we show that the VCD modes of an achiral water molecule after complex formation acquire significant rotational strengths whose signs change in line with the geometry of the complex. Moreover, for some water arrangements the VCD spectra can be sensitive to water-wagging conformers and, in temperatures low enough, the intensive nu(OmicronEtaWfree) and beta(H2O) VCD bands may be sufficiently separated to be splitted into pair of oppositely directed bands. 相似文献
13.
K. J. Jalkanen Julian D. Gale P. R. Lassen L. Hemmingsen A. Rodarte I. M. Degtyarenko R. M. Nieminen S. Brøgger Christensen M. Knapp-Mohammady S. Suhai 《Theoretical chemistry accounts》2008,119(1-3):177-190
In this work we present the experimental and theoretical vibrational absorption (VA) and the theoretical vibrational circular
dichroism (VCD) spectra for aframodial. In addition, we present the theoretical VA and VCD spectra for the diasteriomers of
aframodial. Aframodial has four chiral centers and hence has 24 = 16 diasteriomers, which occur in eight pairs of enantiomers. In addition to the four chiral centers, there is an additional
chirality due to the helicity of the entire molecule, which we show by presenting 12 configurations of the 5S,8S,9R,10S enantiomer
of aframodial. The VCD spectra for the diasteriomers and the 12 configurations of one enantiomer are shown to be very sensitive
not only to the local stereochemistry at each chiral center, but in addition, to the helicity of the entire molecule. Here
one must be careful in analyzing the signs of the VCD bands due to the ‘non-chiral’ chromophores in the molecule, since one
has two contributions; one due to the inherent chirality at the four chiral centers, and one due to the chirality of the side
chain groups in specific conformers, that is, its helicity. Theoretical simulations for various levels of theory are compared
to the experimental VA recorded to date. The VCD spectra simulations are presented, but no experimental VCD and Raman spectra
have been reported to date, though some preliminary VCD measurements have been made in Stephens’ lab in Los Angeles. The flexible
side chain is proposed to be responsible for the small size of the VCD spectra of this molecule, even though the chiral part
of the molecule is very rigid and has four chiral centers. In addition to VCD and Raman measurements, Raman optical activity
(ROA) measurements would be very enlightening, as in many cases bands which are weak in both the VA and VCD, may be large
in the Raman and/or ROA spectra. The feasibility of using vibrational spectroscopy to monitor biological structure, function
and activity is a worthy goal, but this work shows that a careful theoretical analysis is also required, if one is to fully
utilize and understand the experimental results. The reliability, reproduceability and uniqueness of the vibrational spectroscopic
experiments and the information which can be gained from them is discussed, as well as the details of the computation of VA,
VCD and Raman (and ROA) spectroscopy for molecules of the complexity of aframodial, which have multiple chiral centers and
flexible side chains.
Festschrift in Honor of Philip J. Stephens’ 65th Birthday. 相似文献
14.
《Tetrahedron: Asymmetry》2014,25(6-7):507-515
NH-Indazoles in solid phase usually form NH⋯N hydrogen bonds between positions 1 and 2, which determine the secondary structure, forming dimers, trimers, or catemers (chains). Thus, the difficulty of the experimental analysis of the structure of the family of 1H-indazoles is clear. We have outlined a complete strategy by using different techniques of vibrational spectroscopy that are sensitive (VCD) and not sensitive (IR, FarIR, and Raman) to the chirality together with quantum chemical calculations. We have studied the chiral structure of (4S,7R)-campho[2,3-c]pyrazole both in solution (CCl4) and in the solid phase (crystal). This compound crystallizes as a chiral trimer (LABHEB), with the monomer also being chiral. Herein, Far-IR, IR, and Raman spectra in solution and in the solid state are assigned using the support of B3LYP/6-31G(d) and B97D/6-31+G(d,p) calculations of (4S,7R)-campho[2,3-c]pyrazole monomers, dimers, and trimers, these last cyclamers being partially and fully optimized. Later, analysis of the vibrational circular dichroism (VCD) spectra allowed us to determine the chiral self-assembly of (4S,7R)-campho[2,3-c]pyrazole crystals (LABHEB). In the crystal, only the trimers are present while in solution, the monomer predominates. We have highlighted the importance of the analysis of the low frequency region (700–25 cm−1) in the FT-Raman and Far-IR spectra, because it provides relevant information in order to confirm the presence of the trimers in the solid phase. 相似文献
15.
Devlin FJ Stephens PJ Osterle C Wiberg KB Cheeseman JR Frisch MJ 《The Journal of organic chemistry》2002,67(23):8090-8096
The chiral monosubstituted derivatives of spiropentane, spiropentylcarboxylic acid methyl ester, 1, and spiropentyl acetate, 2, have been synthesized in optically active form. Configurational and conformational analysis of 1 and 2 has been carried out using infrared (IR) and vibrational circular dichroism (VCD) spectroscopies. Analysis of the experimental IR and VCD spectra has been carried out using ab initio density functional theory (DFT). For both 1 and 2, DFT predicts two populated conformations. Comparison to experiment of the conformationally averaged IR and VCD spectra of 1 and 2, predicted using DFT, provides unequivocal evidence of the predicted conformations and yields the absolute configurations R(-)/S(+) for 1 and R(+)/S(-) for 2. These absolute configurations are consistent with the R(-)/S(+) absolute configuration of spiropentylcarboxylic acid, assigned previously via X-ray crystallography of its alpha-phenylethylammonium salt. 相似文献
16.
To understand or identify whether a dimer forms or not derived from a chiral compound via H-bonds in solution is critically important. In our previous study, sotolon 1 has two methyl groups, it can form dimers in solution, but maple furanone 2, derived from 1, has one ethyl group and one methyl group, it cannot form dimer. This could be checked by using chiroptical spectroscopies of optical rotation (OR), electronic circular dichroism (ECD) and vibrational circular dichroism (VCD). In this study, four methods was used for the chiral α-hydroxyl ketones and esters (3–8). B3LYP and MPW1PM91 methods with four sets were used to calculate OR, ECD and VCD. The theoretical results exhibited that VCD method could provide more details and promises to ultimately distinguish between the presence of monomer or dimer in solution. 相似文献
17.
Naubron JV Giordano L Fotiadu F Bürgi T Vanthuyne N Roussel C Buono G 《The Journal of organic chemistry》2006,71(15):5586-5593
The enantiomers of tert-butyl(dimethylamino)phenylphosphine-borane complex 2 have been separated by HPLC using cellulose tris-p-methylbenzoate as chiral stationary phase. The borane protection could be removed without racemization and the P-configuration of the free aminophosphine 1 has shown to be stable in solution. Infrared (IR) and vibrational circular dichroism (VCD) spectra have been measured in CD2Cl2 solution for both enantiomers. B3LYP/6-31+G(d) DFT calculations allowed a prediction that complex (S)-2 exists as three conformers in equilibrium and computed population-weighted IR and VCD spectra. Predicted and experimental IR and VCD spectra compared very well and indicate that enantiomer (+)-2 has the S absolute configuration. This assignment has been confirmed by an X-ray diffraction study on a single crystal of (+)-2. The crystal structure of enantiomerically pure 2 appears to be very close to the most stable computed conformer which proved to be predominant in solution. 相似文献
18.
The infrared vibrational absorption (VA) and vibrational circular dichroism (VCD) spectra of methyl lactate were measured in the 1000-1800 cm(-1) region in the CCl(4) and H(2)O solvents, respectively. In particular, the chirality transfer effect, i.e. the H-O-H bending bands of the achiral water subunits that are hydrogen-bonded to the methyl lactate molecule exhibit substantial VCD strength, was detected experimentally. A series of density functional theory calculations using B3PW91 and B3LYP functionals with 6-311++G(d,p) and aug-cc-pVTZ basis sets were carried out to simulate the VA and VCD spectra of the methyl lactate monomer and the methyl lactate-(H(2)O)(n) complexes with n = 1, 2, 3. The population weighted VA and VCD spectra of the methyl lactate monomer are in good agreement with the experimental spectra in CCl(4). Implicit polarizable continuum model was found to be inadequate to account for the hydrogen-bonding effect in the observed VA and VCD spectra in H(2)O. The methyl lactate-(H(2)O)(n) complexes with n = 1, 2, 3 were used to model the explicit hydrogen-bonding. The population weighted VA and VCD spectra of the methyl lactate-H(2)O binary complex are shown to capture the main spectral features in the observed spectra in aqueous solution. The theoretical modeling shows that the extent of chirality transfer depends sensitively on the specific binding sites taken by the achiral water molecules. The observation of chirality transfer effect opens a new spectral window to detect and to model the hydrogen-bonding solvent effect on VCD spectra of chiral molecules. 相似文献
19.
Sadlej J Dobrowolski JC Rode JE Jamróz MH 《Physical chemistry chemical physics : PCCP》2006,8(1):101-113
This paper presents a discussion of the interaction energies, conformations, vibrational absorption (VA, harmonic and anharmonic) and vibrational circular dichroism (VCD) spectra for conformers of monomeric chiral d(-)-lactic acid and their complexes with water at the DFT(B3LYP)/aug-cc-pVDZ and DFT(B3LYP)/aug-cc-pVTZ levels. A detailed analysis has been performed principally for the two most stable complexes with water, differing by lactic acid conformation. The VCD spectra were found to be sensitive to conformational changes of both free and complexed molecules, and to be especially useful for discriminating between different chiral forms of intermolecular hydrogen bonding complexes. In particular, we show that the VCD modes of an achiral water molecule after complex formation acquire significant rotational strengths whose signs change in line with the geometry of the complex. Using the theoretical prediction, we demonstrate that the VCD technique can be used as a powerful tool for structural investigation of intermolecular interactions of chiral molecules and can yield information complementary to data obtained through other molecular spectroscopy methods. 相似文献
20.
Vibrational circular dichroism (VCD) spectroscopy has a unique specificity to chirality and is highly sensitive to the conformational equilibria of chiral molecules. On the other hand, the matrix‐isolation (MI) technique allows substantial control over sample compositions, such as the sample(s)/matrix ratio and the ratio among different samples, and yields spectra with very narrow bandwidths. We combined VCD spectroscopy with the MI technique to record MI‐VCD and MI‐vibrational absorption spectra of 3‐butyn‐2‐ol at different MI temperatures, which allowed us to investigate the conformational distributions of its monomeric and binary species. Good mirror‐imaged MI‐VCD spectra of opposite enantiomers were achieved. The related conformational searches were performed for the monomer and the binary aggregate and their vibrational absorption and VCD spectra were simulated. The well‐resolved experimental MI‐VCD bands provide the essential mean to assign the associated vibrational absorption spectral features correctly to a particular conformation in case of closely spaced bands. By varying the matrix temperature, we show that one can follow the self‐aggregation process of 3‐butyn‐2‐ol and confidently correlate the MI‐VCD spectral features with those obtained for a 0.1 M CCl4 solution and as a neat liquid at room temperature. Comparison of the aforementioned experimental VCD spectra shows conclusively that there is a substantial contribution from the 3‐butyn‐2‐ol aggregate even at 0.1 M concentration. This spectroscopic combination will be powerful for studying self‐aggregation of chiral molecules, and chirality transfer from a chiral molecule to an interacting achiral molecule and in electron donor–acceptor chiral complexes. 相似文献