Conformational instability upon dimerization: Prolinol

Lee, Juhyon J.; Hesse, Susanne; Suhm, Martin A.

doi:10.1016/j.molstruc.2010.03.052

Cited by 10 publications

(14 citation statements)

References 34 publications

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“…Similar conformation change upon complex formation or dimerization is reported in benzo-15-crown-5 (B15C5)-(H 2 O) n complexes [45] and other flexible molecules, in which OH···O and OH···N are key interactions. [58,59] The characteristic of the boat-DB18C6-(H 2 O) 1 complex is that the water molecule in the cavity forms bidentate and bifurcated hydrogen bonds to O 1 , O 3 , O 4 , and O 6 atoms of DB18C6, which makes the boat conformation very stable.…”

Section: Inclusion Complexes Of Benzene-substituted Crown Ethers Withmentioning

confidence: 99%

Laser Spectroscopic Study of Cold Host–Guest Complexes of Crown Ethers in the Gas Phase

et al. 2012

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A laser spectroscopic study on the structure and dynamics of cold host-guest inclusion complexes of crown ethers (CEs) with various neutral and ionic species in the gas phase is presented. The complexes with neutral guest species are formed by using supersonic free jets, and those with ionic species are generated with electrospray ionization combined with a cold 22-pole ion trap. For CEs, various sizes of 3n-crown-n ethers (n=4, 5, 6, and 8) and their benzene-substituted species are used. For the guest species, water, methanol, ammonia, acetylene, and phenol are employed as neutral guest species, and for charged guest species, alkali metal cations are chosen. The electronic and vibrational spectra of the complexes are measured by using various laser spectroscopic methods; electronic spectra for the neutral complexes are measured by laser-induced fluorescence. Discrimination of different species such as conformers is performed by ultraviolet-ultraviolet hole-burning spectroscopy. The vibrational spectra of selected species are observed by infrared-ultraviolet double-resonance (IR-UV DR) spectroscopy. For the ionic complexes, ultraviolet photodissociation and IR-UV DR spectroscopy are applied. The complex structures are determined by comparing the observed spectra with those of possible structures obtained by density functional theory calculations. How the host CEs change their conformation or which conformer prefers to form unique inclusion complexes are discussed. These results reveal the key interactions for forming special complexes leading to molecular recognition.

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Section: Inclusion Complexes Of Benzene-substituted Crown Ethers Withmentioning

confidence: 99%

Laser Spectroscopic Study of Cold Host–Guest Complexes of Crown Ethers in the Gas Phase

et al. 2012

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“…Descriptions of the basic experimental setup may be found in Refs. [19][20][21]. At variance with this earlier work, helium as a carrier gas was first guided through a temperaturecontrolled saturator containing the volatile liquid (i.e., water, methanol) at a temperature ϑ before being admitted into the heated substance chamber containing imidazolecovered molecular sieve at a temperature θ .…”

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confidence: 99%

Communication: Where does the first water molecule go in imidazole?

Zischang

Lee

Suhm

2011

The Journal of Chemical Physics

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Supersonic jet FTIR spectroscopy supplemented by 18O substitution shows unambiguously that water prefers to act as an O−H⋅⋅⋅N hydrogen bond donor towards imidazole, instead of acting as a N−H⋅⋅⋅O acceptor. Previous matrix isolation, helium droplet, and aromatic substitution experiments had remained ambiguous, as are standard quantum chemical calculations. The finding is supported by a study of the analogous methanol complexes and by higher level quantum chemical calculations.

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“…Previous results have shown that the proton is located on the α‐amino nitrogen of alanine . However, it has been shown that gas‐phase complexes can contain subunits that are not the most stable form of the bare entity …”

Section: Experimental and Computational Methodsmentioning

confidence: 98%

“…38 However, it has been shown that gas-phase complexes can contain subunits that are not the most stable form of the bare entity. 20,[52][53][54] Therefore, three sets of exploration of the potential energy surface were launched, with the proton located on NH 2 , OH, and CO, respectively. After each of them, the 20 most stable conformers were optimized at the b3lyp/6-31++G(d,p) level of theory using the Gaussian 09 package.…”

Section: Theoretical Methodsmentioning

confidence: 99%

Mass Spectrometry Study and Infrared Spectroscopy of the Complex Between Camphor and the Two Enantiomers of Protonated Alanine: The Role of Higher‐Energy Conformers in the Enantioselectivity of the Dissociation Rate Constants

et al. 2013

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The properties of the protonated complexes built from S camphor and R or S alanine were studied in a Paul ion trap at room temperature by collision-induced dissociation (CID) and infrared multiple-photon dissociation spectroscopy (IRMPD), as well as molecular dynamics and ab initio calculations. While the two diastereomer complexes display very similar vibrational spectra in the fingerprint region, in line with similar structures, and almost identical calculated binding energies, their collision-induced dissociation rates are different. Comparison of the IRMPD results to computed spectra shows that the SS and SR complexes both contain protonated alanine strongly hydrogen-bonded to the keto group of camphor. The floppiness of this structure around the NH⁺...O=C hydrogen bond results in a complex potential energy surface showing multiple minima. Calculating the dissociation rate constant within the frame of the transition state theory shows that the fragmentation rate larger for the heterochiral SR complex than the homochiral SS complex can be explained in terms of two almost isoenergetic low-energy conformers in the latter that are not present for the former.

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Conformational instability upon dimerization: Prolinol

Cited by 10 publications

References 34 publications

Laser Spectroscopic Study of Cold Host–Guest Complexes of Crown Ethers in the Gas Phase

Laser Spectroscopic Study of Cold Host–Guest Complexes of Crown Ethers in the Gas Phase

Communication: Where does the first water molecule go in imidazole?

Mass Spectrometry Study and Infrared Spectroscopy of the Complex Between Camphor and the Two Enantiomers of Protonated Alanine: The Role of Higher‐Energy Conformers in the Enantioselectivity of the Dissociation Rate Constants

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