Conformational analysis of jet-cooled tryptophan analogs by rotational coherence spectroscopy

Connell, L. L.; Corcoran, Timothy C.; Joireman, P.; Felker, Peter

doi:10.1016/0009-2614(90)87143-f

Cited by 54 publications

(43 citation statements)

References 34 publications

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“…A similar behavior was observed for A + G − G − in group G − and for CTG − in group T´(Figs. S1 and S2, respectively) thus showing that, given a similar electric environment, the better LP N10 donor role is associated to a less negative V(r) on N 10 .…”

Section: Donormentioning

confidence: 83%

“…A variety of spectroscopic techniques combined with supersonic expansion, were employed in order to obtain information on its conformational flexibility. An extensive set of studies of the ultraviolet spectroscopy of jet cooled tryptamine and other tryptophan derivatives were carried out in the past identifying a total of seven conformers [7][8][9][10][11]. Then, experimental studies with resonant ion-dip infrared and UV-UV hole burning spectroscopies were combined with density functional theory (DFT) calculations and nine conformers were described theoretically [12,13].…”

Section: Introductionmentioning

confidence: 99%

“…There is a wide availability of experimental data on the conformers of TRA in the gas phase [6][7][8][9][10][11][12][13][14]. A variety of spectroscopic techniques combined with supersonic expansion, were employed in order to obtain information on its conformational flexibility.…”

Section: Introductionmentioning

confidence: 99%

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Conformational and stereoelectronic investigation of tryptamine. An AIM/NBO study

et al. 2011

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atoms in molecules) and natural bond orbital (NBO) framework was performed. The study was enriched by a deep analysis of maps of molecular electrostatic potential (MEP) through a coordinated NBO/AIM analysis. The conformational preferences were explained by hyperconjugative interactions, which were revealed by NBO data. Because radical scavenging by indolic compounds is strongly modulated by their functional residues our study was related to similar analysis done previously on Indole and 1H-indole-3-acetic acid (IAA). Therefore, the conformational space of TRA was studied from a new perspective focusing on a deep analysis of the geometric and electronic properties of TRA conformers. The changes of the electronic distribution introduced by the substituent and the conformational flexibility of the side chain were addressed. The results reported contribute to the understanding of the structure, stability and reactivity of TRA and others indole derivatives.

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Section: Donormentioning

confidence: 83%

Section: Introductionmentioning

confidence: 99%

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Conformational and stereoelectronic investigation of tryptamine. An AIM/NBO study

et al. 2011

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“…Subsequently, partially resolved contours of these bands [3,4] and those of deuterated tryptamine [5] were used to assign the various conformers of TRA. Rotational coherence measurements extended the analysis and also identified a water complex of TRA [6][7][8][9]. A more detailed conformational profile was given once R2PI, RIDIR and UV-UV hole burning investigations were combined with the results from previous studies [10].…”

Section: Introductionmentioning

confidence: 99%

Tryptamine in the gas phase. A high resolution laser study of the structural and dynamic properties of its ground and electronically excited states

Nguyen¹,

Korter²,

Pratt³

2005

Molecular Physics

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High resolution S 1 S 0 fluorescence excitation spectra of tryptamine have been observed in the collision-free environment of a supersonic molecular beam. Each origin band has been assigned to a unique conformer of the isolated molecule based on its observed rotational constants. For the first time, subbands have been detected in the rotationally resolved spectra of bands C blue and D. A possible hindered motion is proposed to account for the appearance of these subbands. This motion connects the minima associated with the Antipy and Antiph conformers, and thus explores new regions of the energy landscape of this important biomolecule.

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“…Connell et al performed an analysis of the conformational landscape using rotational coherence spectroscopy. 5 The A and B conformers of tryptamine have been observed using microwave spectroscopy. 16 In this study no further conformers could be found.…”

Section: Introductionmentioning

confidence: 99%

Electronically excited states of tryptamine and its microhydrated complex

Schmitt

Brause

Marian

et al. 2006

The Journal of Chemical Physics

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The lowest electronically excited singlet states of tryptamine and the tryptamine ͑H 2 O͒ 1 cluster have been studied, using time dependent density functional theory for determination of the geometries and multireference configuration interaction for the vertical and adiabatic excitation energies, the permanent dipole moments, and the transition dipole moment orientations. All molecular properties of the seven experimentally observed conformers of tryptamine could be reproduced with high accuracy. A strong solvent reorientation has been found upon electronic excitation of the 1:1 water cluster of tryptamine to the L a and L b states. The adiabatically lowest excited singlet state in case of the tryptamine monomer is the L b state, while for the 1:1 water complex, the L a is calculated below the L b state.

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Conformational analysis of jet-cooled tryptophan analogs by rotational coherence spectroscopy

Cited by 54 publications

References 34 publications

Conformational and stereoelectronic investigation of tryptamine. An AIM/NBO study

Conformational and stereoelectronic investigation of tryptamine. An AIM/NBO study

Tryptamine in the gas phase. A high resolution laser study of the structural and dynamic properties of its ground and electronically excited states

Electronically excited states of tryptamine and its microhydrated complex

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