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Special Issue "Reactions in Water"

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A special issue of Molecules (ISSN 1420-3049).

Deadline for manuscript submissions: closed (31 January 2012)

Special Issue Editor

Guest Editor
em. Prof. Dr. Jan B.F.N. Engberts

Stratingh Institute, University of Groningen, Nijenborgh 4, 9747 AG Groningen, The Netherlands
Interests: chemistry in water; hydrophobic interactions; catalysis in water; chemistry of amphiphiles; gene delivery by vesicles

Special Issue Information

Dear Colleagues,

Whereas the single water molecular has no perculiar properties apart from being very small, it is the aqueous liquid, with its highly dynamic three-dimensional hydrogen-bond network, that has many unique properties. All living systems are critically dependent on the presence of water, both as a medium and as a reagent. In physical-organc chemistry it is often the medium of choice, in part because of its high dielectric constant that avoids ion pair formation and the associated kinetic complexities. Although being the ultimate green solvent, in synthetic chemistry water has for a long time not been popular for two main reasons: (1) the limited solubility of  many apolar substrates and (2) the instability of  a variety of functional groups in aqueous media.

In the past three decades there have been many new developments. Kinetic studies, performed at low substrate concentrations, showed that hydrophobic effects had highly interesting effects both on the reactivity of apolar substrates in water as well as on the stereochemistry of these reactions. Particularly pericyclic reactions have been examined in considerable detail. A second breakthrough came from the group of Sharpless. In contrast with traditional beliefs, it was found that the limited solubilities of organic substrates can be turned into an advantage. A number of transformations, conducted in heterogeneous aqueous suspensions, showed high yields, often improved reaction rates and favorable stereochemistry. Such “on-water reactions” opened many novel possibilities for powerful synthetic protocols in water and for mechanistic investigations.

“Reactions in Water” remains a highly challenging topic for further investigation of the secrets that the aqueous medium has to offer to present day scientists in the area. I kindly invite my colleagues to submit their novel results to the Special Issue of Molecules. We are eagerly awaiting your contributions!

Dr. Jan B.F.N. Engberts
Guest Editor

Keywords

  • organic, inorganic and  organometallic reactions in water
  • mechanism of reactions in water
  • hydrophobic effects on organic reactivity
  • water, the ultimate green solvent for chemical transformations
  • (bio)catalytic processes in water
  • (stereo)selective reactions in water
  • reactions in highly aqueous mixed solvents
  • “On-water reactions”, mechanism and synthetic applications
  • molecular recognition chemistry in water
  • systems chemistry in water
  • aqueous reactivity of apolar substrates undergoing self-coiling
  • catalysis by surfactant aggregates and cyclodextrines in water
  • microwave-assisted aqueous reactions
  • reactions in supercritical water

Published Papers (3 papers)

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Research

Open AccessArticle The Role of Water in Lanthanide-Catalyzed Carbon–Carbon Bond Formation
Molecules 2012, 17(2), 2073-2081; doi:10.3390/molecules17022073
Received: 26 January 2012 / Revised: 10 February 2012 / Accepted: 14 February 2012 / Published: 20 February 2012
Cited by 10 | PDF Full-text (258 KB)
Abstract
Luminescence-decay measurements in combination with high-performance liquid chromatography analyses were used to study the relationship between rates of catalysis and water-coordination numbers of europium-based precatalysts in the aqueous Mukaiyama aldol reaction. A correlation between reactivity and water-coordination number was observed and is [...] Read more.
Luminescence-decay measurements in combination with high-performance liquid chromatography analyses were used to study the relationship between rates of catalysis and water-coordination numbers of europium-based precatalysts in the aqueous Mukaiyama aldol reaction. A correlation between reactivity and water-coordination number was observed and is reported here. Full article
(This article belongs to the Special Issue Reactions in Water)
Open AccessArticle Study of the Reaction 2-(p-Nitrophenyl)ethyl Bromide + OH in Dimeric Micellar Solutions
Molecules 2011, 16(11), 9467-9479; doi:10.3390/molecules16119467
Received: 13 October 2011 / Revised: 31 October 2011 / Accepted: 8 November 2011 / Published: 11 November 2011
Cited by 1 | PDF Full-text (232 KB)
Abstract
The dehydrobromination reaction 2-(p-nitrophenyl)ethyl bromide + OH was investigated in several alkanediyl-a-w-bis(dodecyldimethylammonium) bromide, 12-s-12,2Br (with s = 2, 3, 4, 5, 6, 8, 10, 12) micellar solutions, in the presence of NaOH 5 × 10−3 M. The [...] Read more.
The dehydrobromination reaction 2-(p-nitrophenyl)ethyl bromide + OH was investigated in several alkanediyl-a-w-bis(dodecyldimethylammonium) bromide, 12-s-12,2Br (with s = 2, 3, 4, 5, 6, 8, 10, 12) micellar solutions, in the presence of NaOH 5 × 10−3 M. The kinetic data were quantitatively rationalized within the whole surfactant concentration range by using an equation based on the pseudophase ion-exchange model and taking the variations in the micellar ionization degree caused by the morphological transitions into account. The agreement between the theoretical and the experimental data was good in all the dimeric micellar media studied, except for the 12-2-12,2Br micellar solutions. In this case, the strong tendency to micellar growth shown by the 12-2-12,2Br micelles could be responsible for the lack of accordance. Results showed that the dimeric micelles accelerate the reaction more than two orders of magnitude as compared to water. Full article
(This article belongs to the Special Issue Reactions in Water)
Open AccessArticle Linear Polystyrene-Stabilized PdO Nanoparticle-Catalyzed Mizoroki-Heck Reactions in Water
Molecules 2011, 16(11), 9067-9076; doi:10.3390/molecules16119067
Received: 19 September 2011 / Revised: 22 October 2011 / Accepted: 26 October 2011 / Published: 27 October 2011
Cited by 13 | PDF Full-text (595 KB)
Abstract
Linear polystyrene-stabilized PdO nanoparticles (PS-PdONPs) were prepared by thermal decomposition of Pd(OAc)2 in the presence of polystyrene. X-ray diffraction (XRD) and transmission electron microscopy (TEM) indicated the production of PdO nanoparticles. The loading of palladium was determined by inductively coupled plasma-atomic [...] Read more.
Linear polystyrene-stabilized PdO nanoparticles (PS-PdONPs) were prepared by thermal decomposition of Pd(OAc)2 in the presence of polystyrene. X-ray diffraction (XRD) and transmission electron microscopy (TEM) indicated the production of PdO nanoparticles. The loading of palladium was determined by inductively coupled plasma-atomic emission spectroscopy (ICP-AES). PS-PdONPs exhibited high catalytic activity for Mizoroki-Heck reactions under air in water and could be recycled without loss of activity. Full article
(This article belongs to the Special Issue Reactions in Water)
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