Recent advances in catalysis have made the incorporation of fluorine into complex organic molecules easier than ever before, but selective, general and practical fluorination reactions remain sought after. Fluorination of molecules often imparts desirable properties, such as metabolic and thermal stability, and fluorinated molecules are therefore frequently used as pharmaceuticals or materials. But the formation of carbon-fluorine bonds in complex molecules is a significant challenge. Here we discuss reactions to make organofluorides that have emerged within the past few years and which exemplify how to overcome some of the intricate challenges associated with fluorination.

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Catalysis for fluorination and trifluoromethylation

Many, if not most, redox reactions are coupled to proton transfers. This includes most common sources of chemical potential energy, from the bioenergetic processes that power cells to the fossil fuel combustion that powers cars. These proton-coupled electron transfer or PCET processes may involve multiple electrons and multiple protons, as in the 4 e–, 4 H+ reduction of dioxygen (O2) to water (eq 1), or can involve one electron and one proton such as the formation of tyrosyl radicals from tyrosine residues (TyrOH) in enzymatic catalytic cycles (eq 2). In addition, many multi-electron, multi-proton processes proceed in one-electron and one-proton steps. Organic reactions that proceed in one-electron steps involve radical intermediates, which play critical roles in a wide range of chemical, biological, and industrial processes. This broad and diverse class of PCET reactions are central to a great many chemical and biochemical processes, from biological catalysis and energy transduction, to bulk industrial chemical processes, to new approaches to solar energy conversion. PCET is therefore of broad and increasing interest, as illustrated by this issue and a number of other recent reviews.

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Thermochemistry of Proton-Coupled Electron Transfer Reagents and its Implications

Cross-coupling reactions using Pd-NHC (NHC = N-heterocyclic carbene) catalysts are discussed in this critical review and examined in terms of catalytic activity and how these have permitted advances in the area as they developed (95 references).

N-Heterocyclic carbene (NHC) ligands and palladium in homogeneous cross-coupling catalysis: a perfect union

Detection Ying Zhou,†,‡ Jun Feng Zhang, and Juyoung Yoon*,† †Department of Chemistry and Nano Science, Ewha Womans University, Seoul 120-750, Korea ‡Key Laboratory of Medicinal Chemistry for Natural Resource, School of Chemical Science and Technology, Yunnan University, Kunming, 650091, P. R. China College of Chemistry and Chemical Engineering, Yunnan Normal University, Kunming 650500, P. R. China

Fluorescence and colorimetric chemosensors for fluoride-ion detection.

Minerals and organic matter (OM) may form intricate associations via myriad interactions. In soils, the associations of OM with mineral surfaces are mainly investigated because of their role in determining the long-term retention of OM. OM “must decay in order to release the energy and nutrients that drive live processes all over the planet” ( Janzen, 2006 ). Thus, the processes and mechanisms that retain OM in soil are a central concern to very different branches of environmental research. An agronomist may want to synchronize periods of high nutrient and energy release with the growth stages of a crop. An environmental chemist may wish to either immobilize an organic soil contaminant or enhance its decomposition into less harmful metabolites, while climate scientists need to understand the processes that mediate the production of potent greenhouse gases from decomposing OM. Associations of OM with pedogenic minerals (henceforth termed mineral–organic associations (MOAs)) are known to be key controls in these and many other processes. Here we strive to present an overview of the current knowledge on MOAs and identify key questions and future research needs.

Chapter One – Mineral–Organic Associations: Formation, Properties, and Relevance in Soil Environments

Introduction Experimental methods for measuring BDEs BDEs of C-H Bonds BDEs of C-C Bonds BDEs of C-halogen bonds BDEs of O-X bonds BDEs of N-X bonds BDEs of S-, Se-, Te-, and Po-X bonds BDEs of Si-, Ge-, Sn-, and Pb-X bonds BDEs of P-, As-, Sb-, and Bi-X bonds BDEs of H(H+/-)-, Li(Li+/-)-, Na(Na+/-)-, K(K+/-)-, Rb(Rb+/-)-, and Cs(Cs+/-)-X bonds BDEs of Be(Be+)-, Mg(Mg+)-, Ca(Ca+)-, Sr(Sr+)-, Ba(Ba+)-, and Ra-X bonds BDEs of Sc(Sc+)-, Y(Y+)-, La(La+)-, and Ac(Ac+)-X bonds BDEs of Ti(Ti+/-)-, Zr(Zr+)-, and Hf(Hf+)-X bonds BDEs of V(V+/-)-, Nb(Nb+)-, and Ta(Ta+)-X bonds BDEs of Cr(Cr+/-)-, Mo(Mo+/-)-, and W(W+/-)-X bonds BDEs of Mn(Mn+/-)-, Tc-, and Re(Re+)-X bonds BDEs of Fe(Fe+/-)-, Ru(Ru+)-, and Os(Os+)-X bonds BDEs of Co(Co+/-)-, Rh(Rh+)-, and Ir(Ir+)-X bonds BDEs of Ni(Ni+/-)-, Pd(Pd+/-)-, and Pt(Pt+/-)-X bonds BDEs of Cu(Cu+/-)-, Ag(Ag+/-)-, and Au(Au+/-)-X bonds BDEs of Zn(Zn+)-, Cd(Cd+)-, and Hg(Hg+)-X bonds BDEs of B(B+/-)-, Al(Al+/-)-, Ga(Ga+/-)-, In(In+/-)-, and Tl(Tl+/-)-X Bonds BDEs in the C-, Si-, Ge-, Sn-, Pb-clusters and complexes BDEs in the N-, P-, As-, Sb-, Bi-clusters and complexes BDEs in the O-, S-, -Se, and Te-clusters and complexes BDEs in the halogenated molecules, clusters, and complexes BDEs in rare gas atom/ion clusters Heats of formation of atoms, radicals, and ions References (1946 through 2006) Index of compound classes Index of compound names

Comprehensive handbook of chemical bond energies

INTRODUCTION A Database of the BDEs What is the BDE? Why We Need Reliable BDEs Scope of this Book On Energy Units How to Search for BDEs in this Book How to Use the Tables of the BDE Data EXPERIMENTAL METHODS FOR MEASURING BDEs TABULATED BDES OF C-H BONDS Chain-Saturated Hydrocarbons Chain-Unsaturated Hydrocarbons Cyclic Hydrocarbons Aromatic Hydrocarbons Halogenated Hydrocarbons Organic Compounds Containing Heteroatoms TABULATED BDES OF C-C BONDS Saturated Hydrocarbons Chain-Unsaturated Hydrocarbons Aromatic Hydrocarbons Halogenated Hydrocarbons Organic Compounds Containing Heteroatoms TABULATED BDES OF C-HALOGEN BONDS C-F Bonds C-Cl Bonds C-Br Bonds C-I Bonds TABULATED BDES OF O-X BONDS O-H Bonds O-O Bonds O-C Bonds O-N Bonds O-S, O-Halogen, and O-P Bonds TABULATED BDES OF N-X BONDS N-H Bonds N-N Bonds N-C Bonds N-S Bonds N-Halogen Bonds TABULATED BDES OF S-X BONDS S-H Bonds S-S Bonds S-C Bonds S-Halogen and S-P Bonds TABULATED BDES OF Si-, Ge-, Sn-, P-, AND Se-X BONDS Si-X Bonds Ge-X Bonds Sn-X Bonds P-X Bonds Se-X Bonds TABULATED BDES IN SOME INORGANIC COMPOUNDS HEATS OF FORMATION OF ATOMS, INORGANIC AND ORGANIC RADICALS Gaseous Atoms Small Inorganic Radicals in the Gas Phase Organic Radicals in the Gas Phase Group Additivity Values for Organic Radicals REFERENCES INDEX OF COMPOUND CLASSES INDEX OF COMPOUND NAMES

Yu-Ran Luo

Papers

Comprehensive handbook of chemical bond energies

Handbook of Bond Dissociation Energies in Organic Compounds

BDEs of Si–, Ge–, Sn–, and Pb–X bonds

BDEs of C–C bonds

Tabulated BDEs of C–C bonds