Chalcogenocarboxylic acid

T. Murai, Topics in Current Chemistry, vol 251, Springer, GmbH, 2005, (Chalcogenocarboxylic Acid Derivatives), 247-272. 

Nicolau DV, Sawant PD (2005) Scanning Probe Microscopy Studies of Surface-Immobilised DNA/Oligonucleotide Molecules. 260 113-160 Niyomura O, Kato S (2005) Chalcogenocarboxylic Acids. 251 1-12 Niyomura O, see Kato S (2005) 251 19-85... 

Chalcogenocarboxylic Acid Derivatives Volume Editor Kato, S. 

Keywords Chalcogenocarboxylic acids Chalcogenol form Chalcogenoxo form Carboxylic acids Chalcogens... 

As shown in Scheme 1, there are 15 kinds of chalcogenocarboxylic acid. There are six monochalcogenocarboxylic acids, that have oxygen and chalco-gen atoms (A), as well as their tautomers (A ). There are also the dichalcogeno-carboxylic acids (B and C), while the dichalcogenocarboxylic acids with two different chalcogen atoms (of which there are three kinds, B) also possess tautomers (B ). 

Historically, the first chalcogenocarboxylic acid discovered was thiocarboxylic acid - thioacetic acid - reported by Kekule in 1854 [1]. Since then, chalcogenocarboxylic acids, and particularly numerous thio- and dithiocarboxylic acid esters, have been synthesized and summarized in several review articles [2-9]. In contrast, until very recently, little has been known about the chemistry of the congeners containing heavier chalcogen atoms, such as selenium and tellurium, probably due to their instability and the handling difficulties associated with them. In this chapter, the chemistry of chalcogenocarboxylic acids, their syntheses, structures, spectral features and reactions are reviewed. 

Little crystallographic information is available on chalcogenocarboxylic acids. Few (if any) thio- [25,26] and dithiocarboxylic acids [25-28] are known, and no congeners containing selenium and tellurium have been found. 

Semiempirical and ab initio theory molecular orbital calculations have been carried out on chalcogenocarboxylic acids, especially simple thiocarboxylic acids... 

Chalcogenocarboxylic acids, especially thio- and dithiocarboxylic acids, have been used as starting materials for synthesizing corresponding chalcogenocarboxylic acid derivatives, and this topic is discussed in greater detail in Chapters 2 and 3. However, at this point we will review some of the most distinctive reactions reported over the last ten years. 

Abstract Over the last two decades, our understanding of the chemistry of Group 1-17 element derivatives of chalcogenocarboxylic acids has improved considerably. In recent years, the structures of these compounds have been revealed using X-ray diffraction. The present review surveys the syntheses, structures and reactions of Group 1-17 element derivatives of thio-, seleno- and telluro-carboxylic acids, except for when carbon is the Group 1-17 element attached directly to the chalcogen atom. 

A series of rubidium thio- 1 (M=Rb) [150], seleno- 4 (M=Rb) [171, 326] and telluro-carboxylates 5 (M=Rb) [174] have been isolated in moderate to good yields from the reactions of the corresponding chalcogenocarboxylic acids or... 

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