Solvent complexes of jet-cooled ?-phenylethylamine

Sipior, Jeffrey; Teh, C. K.; Sulkes, Mark

doi:10.1007/bf00865257

Cited by 15 publications

(33 citation statements)

References 13 publications

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“…PEA clustered with CH 4 , CF 4 , and CF 3 Cl shows binding behavior similar to that of PEA(Ar) 1 (Table 6), with the most stable isomers assuming a ring TOP structure. The reduced symmetry of CF 3 Cl causes several additional local minimum structures for each type of general binding structure; these differ only by the change of CF 3 Cl orientation with respect to the PEA conformer.…”

Section: Resultsmentioning

confidence: 54%

“…This additional interaction results in significantly higher binding energies for PEAC(CF 3 H) 1 and PEAC(CF 2 H 2 ) 1 clusters compared to those for PEAA at this SIDE position, as seen from Table 6. The PEAC binding energies for these solvents can become as high as, or even higher than, those for the TOP binding positions of the other (PEAA) conformers.…”

Section: Resultsmentioning

confidence: 84%

“…Like PEA(CF 3 Cl) 1 , PEA clustered with CF 3 H and CF 2 H 2 shows multiple local minima for each of the TOP, BOTTOM, and SIDE binding types; however, additional binding can arise for PEAC(CF 3 H) 1 and PEAC(CF 2 H 2 ) 1 between F atoms of the solvent and H atoms of the phenyl ring ( Figure 3), arising from the high fluorine negative charges for CF 3 H and CF 2 H 2 (ca.…”

Section: Resultsmentioning

confidence: 97%

“…A careful cluster formation and fragmentation study demands very detailed analysis of mass-resolved excitation spectra collected in the cluster parent mass channel (if possible) and in all possible fragment mass channels. As a continuation of the work of Dickinson et al, 5 a recent report by Hockridge et al 6 details the fragmentation of PEA(H 2 O) 1 clusters. Both theory and experiment are presented in this latter reference, and some cluster structural information can be suggested.…”

Section: Introductionmentioning

confidence: 90%

“…3 kcal/mol, one cannot have very high confidence in the accuracy of the solvation properties for PEA thus calculated, although they appear to be qualitatively correct. For systems such as PEA-(Ar) 1 and PEA(CH 4 ) 1 , the cluster binding is much weaker and thus more difficult to calculate from the ab initio approach. 11 A good ab initio estimation of such weak interactions is still beyond current capabilities for systems with so many heavy atoms.…”

Section: Introductionmentioning

confidence: 99%

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Spectroscopy of Neurotransmitters and Their Clusters: Phenethylamine and Amphetamine Solvation by Nonpolar, Polar, and Hydrogen-Bonding Solvents

Yao

Foltin

et al. 2000

J. Phys. Chem. A

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Clusters containing a phenylethylamine (PEA) or amphetamine (AMP) molecule and a solvent species such as Ar, CH 4 , CF 3 H, CO 2 , H 2 O, and other small molecules are formed in a supersonic jet expansion. Spectral studies of the solvation and related chemistry of PEA and AMP are pursued by using both fluorescence and mass spectroscopy techniques. To help analyze the experimental results, ab initio and atom-atom LennardJones-Coulomb (LJC) potential calculations are employed to calculate cluster geometries and binding energies. The LJC potential parameters for the 10-12 hydrogen-bonding potentials have been reevaluated on the basis of new ab initio partial atomic charge values and new experimental binding energies and geometries. The observed dependence of the relative spectral intensities of PEA and AMP conformers and their clusters on the cooling conditions (backing pressure and coolants employed) suggests that these species undergo population redistribution in the cooling and clustering process. The amount of excess energy (binding energy) available to the forming cluster plays a major role in the conformational conversion of PEA and AMP during cluster formation. If strong interactions (hydrogen bonding) exist between the solute and the solvent, such conversion/ redistribution processes occur among all conformers and their clusters. The conversion/redistribution process is restricted within the anti or gauche conformer sets and their clusters for weakly interacting solute/solvent pairs. All PEA and AMP clusters studied experience complete fragmentation upon ionization. The observed gradual dependence of photo ion intensity on the ionization laser energy suggests a significant change in geometry for both PEA and AMP, as well as their clusters, upon ionization. Consequently the high vertical ionization energy leads to an excess energy in the vibrational modes of the ions, causing fragmentation of the clusters. The clusters can fragment along two different general paths: (1) simple loss of the solvent molecules and (2) breaking the R-carbon bond of PEA or AMP, with additional loss of solvent molecules in some cases. Those clusters with weaker solute/solvent binding tend to fragment through solvent loss, while those forming hydrogen bonds tend to favor the R-carbon bond cleavage. Reactions are observed for PEA and AMP with NO. NO can completely quench PEA and AMP monomer spectra.

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Section: Resultsmentioning

confidence: 54%

Section: Resultsmentioning

confidence: 84%

Section: Resultsmentioning

confidence: 97%

Section: Introductionmentioning

confidence: 90%

Section: Introductionmentioning

confidence: 99%

See 3 more Smart Citations

Spectroscopy of Neurotransmitters and Their Clusters: Phenethylamine and Amphetamine Solvation by Nonpolar, Polar, and Hydrogen-Bonding Solvents

Yao

Foltin

et al. 2000

J. Phys. Chem. A

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Effects of Aromatic Fluorine Substitution on Protonated Neurotransmitters: The Case of 2‐Phenylethylamine

Schütz

Bouchet

Chiavarino

et al. 2016

Chemistry A European J

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Fluorination of pharmaceutical compounds is a common tool to modulate their physiochemical properties. We determine the effects of site-specific aromatic fluorine substitution on the geometric, energetic, vibrational, and electronic properties of the protonated neurotransmitter 2-phenylethylamine (xF-H(+) PEA, x=ortho, meta, para) by infrared multiphoton photodissociation (IRMPD) in the fingerprint range (600-1750 cm(-1) ) and quantum chemical calculations at the B3LYP-D3/aug-cc-pVTZ level. The IRMPD spectra of all ions are assigned to their folded gauche conformers stabilized by intramolecular NH(+) ⋅⋅⋅π hydrogen bonds (H-bonds) between the protonated amino group and the aromatic ring. H→F substitution reduces the symmetry and allows for additional NH(+) ⋅⋅⋅F interactions in oF-H(+) PEA, leading to three distinct gauche conformers. In comparison to oF-H(+) PEA, the fluorination effects on the energy landscape (energy ordering and isomerization barriers) in pF-H(+) PEA and mF-H(+) PEA with one and two gauche conformers are less pronounced. The strengths of the intramolecular NH(+) ⋅⋅⋅F and NH(+) ⋅⋅⋅π bonds are analyzed by the noncovalent interaction (NCI) method.

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Conformations of 2-phenylethanol and its singly hydrated complexes: UV–UV and IR–UV ion-dip spectroscopy

Mons

Robertson

Snoek

et al. 1999

Chemical Physics Letters

113

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Solvent complexes of jet-cooled ?-phenylethylamine

Cited by 15 publications

References 13 publications

Spectroscopy of Neurotransmitters and Their Clusters: Phenethylamine and Amphetamine Solvation by Nonpolar, Polar, and Hydrogen-Bonding Solvents

Spectroscopy of Neurotransmitters and Their Clusters: Phenethylamine and Amphetamine Solvation by Nonpolar, Polar, and Hydrogen-Bonding Solvents

Effects of Aromatic Fluorine Substitution on Protonated Neurotransmitters: The Case of 2‐Phenylethylamine

Conformations of 2-phenylethanol and its singly hydrated complexes: UV–UV and IR–UV ion-dip spectroscopy

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