Site of protonation and conformational effects on gas-phase basicity in .beta.-amino alcohols. The nature of internal hydrogen bonding in .beta.-hydroxy ammonium ionsClick to copy article linkArticle link copied!
Note: In lieu of an abstract, this is the article's first page.
Cited By
This article is cited by 36 publications.
- Peng Wei, Kaidi Guo, Wanfen Pu, Yahong Xie, Xueli Huang, Junlan Zhang. Aqueous Foam Stabilized by an in Situ Hydrophobic Polymer via Interaction with Alkyl Polyglycoside for Enhancing Oil Recovery. Energy & Fuels 2020, 34
(2)
, 1639-1652. https://doi.org/10.1021/acs.energyfuels.9b03977
- Xin Chen,, David A. Walthall, and, John I. Brauman. Acidities in Cyclohexanediols Enhanced by Intramolecular Hydrogen Bonds. Journal of the American Chemical Society 2004, 126
(39)
, 12614-12620. https://doi.org/10.1021/ja049780s
- John E. Baldwin and, Rajesh Shukla. Thermal Isomerizations of 1,1-Dimethyl-2,2-d2-cyclopropane. The Journal of Physical Chemistry A 1999, 103
(39)
, 7821-7825. https://doi.org/10.1021/jp9918712
- Scott A. Shaffer, Jill K. Wolken, František Tureček. Neutralization-Reionization of alkenylammonium cations: An experimental and ab initio study of intramolecular N-H … C=C interactions in cations and hypervalent ammonium radicals. Journal of the American Society for Mass Spectrometry 1997, 8
(11)
, 1111-1123. https://doi.org/10.1016/S1044-0305(97)00184-0
- Viet Q. Nguyen and, František Tureček. Protonation Sites in Pyrimidine and Pyrimidinamines in the Gas Phase. Journal of the American Chemical Society 1997, 119
(9)
, 2280-2290. https://doi.org/10.1021/ja9634785
- John W. McKieman, Christina E. A. Beltrame, Carolyn J. Cassady. Gas-phase basicities of serine and dipeptides of serine and glycine. Journal of the American Society for Mass Spectrometry 1994, 5
(8)
, 718-723. https://doi.org/10.1016/1044-0305(94)80003-0
- Guy Bouchoux, Jean‐Yves Salpin. Gas‐phase basicities of polyfunctional molecules. Part 2: Saturated basic sites. Mass Spectrometry Reviews 2012, 31
(3)
, 353-390. https://doi.org/10.1002/mas.20343
- Alessandra Lattanzi. α,α-Diarylprolinols: bifunctional organocatalysts for asymmetric synthesis. Chemical Communications 2009, 43
(12)
, 1452. https://doi.org/10.1039/b900098d
- Alessio Russo, Alessandra Lattanzi. Asymmetric Epoxidation of
trans
‐Chalcones Organocatalyzed by β‐Amino Alcohols. European Journal of Organic Chemistry 2008, 2008
(16)
, 2767-2773. https://doi.org/10.1002/ejoc.200800140
- Giovanni A Pallante, Carolyn J Cassady. Effects of peptide chain length on the gas-phase proton transfer properties of doubly-protonated ions from bradykinin and its N-terminal fragment peptides. International Journal of Mass Spectrometry 2002, 219
(1)
, 115-131. https://doi.org/10.1016/S1387-3806(02)00556-0
- Guy Bouchoux, Nadège Choret, Florence Berruyer-Penaud, Robert Flammang. Thermochemistry and unimolecular reactivity of protonated α,ω-aminoalcohols in the gas phase. International Journal of Mass Spectrometry 2002, 217
(1-3)
, 195-230. https://doi.org/10.1016/S1387-3806(02)00577-8
- Vladimir G. Zaikin, Roman S. Borisov. Stereospecific Ion—molecule Reactions in the
Trans
-Decahydro-4-Hydroxyquinoline Series upon Chemical Ionization. European Journal of Mass Spectrometry 2002, 8
(2)
, 139-145. https://doi.org/10.1255/ejms.482
- M. Edelson-Averbukh, A. Mandelbaum. Stereospecific elimination of dihydropyran from protonated tetrahydropyranyl (THP) difunctional derivatives upon chemical ionization and collision-induced dissociation: intramolecular interactions in polyfunctional ions. International Journal of Mass Spectrometry 2001, 210-211 , 545-556. https://doi.org/10.1016/S1387-3806(01)00417-1
- Tibor Bart�k, Gy�rgy Sz�ll�si, K�roly Felf�ldi, Mih�ly Bart�k, Jacek Thiel. New results on the mass spectra of cinchona alkaloids. Journal of Mass Spectrometry 2000, 35
(6)
, 711-717. https://doi.org/10.1002/1096-9888(200006)35:6<711::AID-JMS998>3.0.CO;2-B
- E. Rathahao, M.C. Perlat, F. Fournier, J.C. Tabet. Stereochemical effects enhanced by using selective “self-ionization” under electron ionization conditions in a quadrupole ion trap mass spectrometer. International Journal of Mass Spectrometry 1999, 193
(2-3)
, 161-179. https://doi.org/10.1016/S1387-3806(99)00109-8
- Ana M. Cardoso, Sílvia M.G. Alexandre, Cristina M.F. Barros, A.J. Ferrer-Correia, N.M.M. Nibbering. Proton affinities of phenylalkylamines by the kinetic method. International Journal of Mass Spectrometry and Ion Processes 1998, 172
(1-2)
, 123-127. https://doi.org/10.1016/S0168-1176(97)00252-8
- Guy Bouchoux, Sylvie Jezequel, Florence Penaud‐Berruyer. Conformational effect on gas‐phase protonation and NH
4
+
clustering of 1,2‐diols. Organic Mass Spectrometry 1993, 28
(4)
, 421-427. https://doi.org/10.1002/oms.1210280426
- Einar Uggerud. Properties and reactions of protonated molecules in the gas phase. Experiment and theory. Mass Spectrometry Reviews 1992, 11
(5)
, 389-430. https://doi.org/10.1002/mas.1280110503
- Shigeru Ikuta, Okio Nomura. An ab initio study on the intramolecular hydrogen bond of protonated ethylene glycol and ethylenediamine. Chemical Physics Letters 1989, 154
(1)
, 71-76. https://doi.org/10.1016/0009-2614(89)87440-8
- Steve Scheiner. Relationship between the angular characteristics of a hydrogen bond and the energetics of proton transfer occurring within. Journal of Molecular Structure 1988, 177 , 79-91. https://doi.org/10.1016/0022-2860(88)80080-2
- R. M. Minyaev, G. V. Orlov. Theoretical study of the dependence of structural parameters of the H bond in the complex NH3H2CO2H+ on position of the proton. Journal of Structural Chemistry 1988, 29
(3)
, 463-466. https://doi.org/10.1007/BF00744005
- Burnaby Munson, Ta‐Min Feng, Harry D. Ward, Roger K. Murray. Isobutane chemical ionization mass spectra of unsaturated alcohols. Organic Mass Spectrometry 1987, 22
(9)
, 606-609. https://doi.org/10.1002/oms.1210220906
- J.C. Tabet, H.E. Audier, J.P. Denhez. Reactions ion-molecule en phase gazeuse. Tetrahedron 1987, 43
(5)
, 873-880. https://doi.org/10.1016/S0040-4020(01)90024-9
- Shigeru Ikuta. Ab initio MO calculations on stabilities and binding energies of bidentate ethylene diamine with ions (Na+, Li+, and H+). Chemical Physics 1986, 108
(3)
, 441-449. https://doi.org/10.1016/0301-0104(86)80111-2
- Guy Bouchoux, Faycal Djazi, Yannik Hoppilliard, Raymond Houriet, Eric Rolli. Gas‐phase protonation of unsaturated ethers: Experimental and theoretical study of 2,3‐and 2,5‐dihydrofuran and related compounds. Organic Mass Spectrometry 1986, 21
(4)
, 209-213. https://doi.org/10.1002/oms.1210210407
- Stanislav N. Tandura, Mikhail G. Voronkov, Nikolai V. Alekseev. Molecular and electronic structure of penta- and hexacoordinate silicon compounds. 1986, 99-189. https://doi.org/10.1007/3-540-15811-1_3
- Raymond Houriet, Thierry Schwitzguebel, Pierre-Alain Carrupt, Pierre Vogel. Experimental and theoretical studies on the homoconjugation in bicyclic carbenium and oxonium ions in the gas phase.. Tetrahedron Letters 1986, 27
(1)
, 37-40. https://doi.org/10.1016/S0040-4039(00)83933-7
- Raymond Houriet, Eric Rolli, Guy Bouchoux, Yannick Hoppilliard. Gas‐Phase Basicities of Furan Compounds. The Role of Alkyl Substitution on Proton Affinity and on the Site of Protonation. Helvetica Chimica Acta 1985, 68
(7)
, 2037-2045. https://doi.org/10.1002/hlca.19850680729
- Christian Guenat, Raymond Houriet, Daniel Stahl, Johann Winkler. Gas‐Phase Basicities of Open‐Chain and Cyclic Diols from Dissociations of Ammonium Adducts, Protonated Mixed Dimers and ICR Experiments. Structural and Stereochemical Effects. Helvetica Chimica Acta 1985, 68
(6)
, 1647-1657. https://doi.org/10.1002/hlca.19850680619
- V.J. Vandiver, C.S. Leasure, G.A. Eiceman. Proton affinity equilibria for polycyclic aromatic hydrocarbons at atmospheric pressure in ion mobility spectrometry. International Journal of Mass Spectrometry and Ion Processes 1985, 66
(2)
, 223-238. https://doi.org/10.1016/0168-1176(85)83012-3
- K. P. Madhusudanan, Shubhra Mittal, Susheel Durani, R. S. Kapil. Stereospecific adduct ion formation in the chemical ionization mass spectra of
E
‐ and
Z
‐1,2,3‐triaryl‐2‐propen‐1‐ones. Organic Mass Spectrometry 1985, 20
(5)
, 323-326. https://doi.org/10.1002/oms.1210200502
- Raymond Houriet, Hermann Rufenacht, Daniel Stahl, Milos Tichy, Pierre Longevialle. Gas phase protonation and subsequent dissociations in β‐amino alcohols as a function of exoergicity and interfunctional distance. Organic Mass Spectrometry 1985, 20
(4)
, 300-304. https://doi.org/10.1002/oms.1210200407
- Jean-Claude Bollinger, Raymond Houriet, Theophile Yvernault. Gas Phase Basicity of Hexamethylphosphotriamide (HMPT) and Phosphinoxide Derivatives. Phosphorus and Sulfur and the Related Elements 1984, 19
(3)
, 379-382. https://doi.org/10.1080/03086648408077603
- K.G. Das, A. Mahender Reddy, M. Vairamani, K.P. Madhusudhanan, D. Fraisse, J.C. Tabet. Reduction of olefinic bond under ammonia chemical ionization. Tetrahedron 1984, 40
(20)
, 4085-4088. https://doi.org/10.1016/0040-4020(84)85089-9
- G. Bouchoux, R. Houriet. Ring size effects on the gas phase protonation of cyclic ketones. Tetrahedron Letters 1984, 25
(50)
, 5755-5758. https://doi.org/10.1016/S0040-4039(01)81678-6
- R. HOURIET, H. + RUEFENACHT, P.‐A. CARRUPT, P. VOGEL, M. TICHY. ChemInform Abstract: SITE OF PROTONATION AND CONFORMATIONAL EFFECTS ON GAS‐PHASE BASICITY IN β‐AMINO ALCOHOLS. THE NATURE OF INTERNAL HYDROGEN BONDING IN β‐HYDROXY AMMONIUM IONS. Chemischer Informationsdienst 1983, 14
(36)
https://doi.org/10.1002/chin.198336136
Article Views are the COUNTER-compliant sum of full text article downloads since November 2008 (both PDF and HTML) across all institutions and individuals. These metrics are regularly updated to reflect usage leading up to the last few days.
Citations are the number of other articles citing this article, calculated by Crossref and updated daily. Find more information about Crossref citation counts.
The Altmetric Attention Score is a quantitative measure of the attention that a research article has received online. Clicking on the donut icon will load a page at altmetric.com with additional details about the score and the social media presence for the given article. Find more information on the Altmetric Attention Score and how the score is calculated.