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Organic Chemistry - Stereoelectronic Effects in Fuel Dehydrating Icing Inhibitors

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Stereoelectronic effects are critically important in the reactivity of ester functional groups like ortho-esters. The primary stereoelectronic effects of ortho esters are particularly caused by the delocalization of electrons between the carboxylic group and the ethereal oxygen during the interaction between ortho esters and free water from the jet fuel.   Stereoelectronic effects are critically important in the reactivity of ester functional groups like ortho-esters. The primary stereoelectronic effects of ortho esters are particularly caused by the delocalization of electrons between the carboxylic group and the ethereal oxygen during the interaction ortho esters and free water from the jet fuel.   Orthoesters are often readily hydrolyzed in mild acid solutions to form esters as the main product.

For example: RC (OR’ ) 3 + H2O → RCO2R’ + 2 R’ OH. This type of ester or the triethyl orthoformate has a chemical formula of RC (OR’ ) 3.  Esters are chemical compounds consisting of both a carbonyl adjacent to an ester linkage. Esters are derived from a reaction of an oxyacid together with the hydroxyl compound such as a phenol or an alcohol. Esters are derived from either inorganic or organic acids through esterification process.

In the esterification reaction at least one – OH (hydroxyl) group is substituted by an – o- alkyl group. This mechanism and interaction of others are commonly experienced from the reaction of alcohol and carboxylic acids. The ortho-esters are therefore formed by condensing an acid with an alcoholic substance. Orthoesters are often naturally occurring oils and fats.   As earlier been noted, stereoelectronic effect plays a critical form a key element on the chemical reactivity of water scavengers. According to Chiang et al.

p. 62), this is particularly attributed to the fact that stereoelectronic factors normally tend to control the rate of chemical reactions as well as the nature of their products.   For example, acetals normally take a conformation where each oxygen atom takes up an electron lone pair antiperiplanar to the carbon-hydrogen (C-H) bond. The actual mechanism of the acid-catalyzed ortho ester hydrolysis is usually comprised of three distinct reaction stages namely: i. Generation of dialkoxy carbonium ions,   ii. Hydration of the generated dialkoxy carbonium ions to hydrogen ortho estersiii. Breakdown of hydrogen into carboxylic acid and alcohol products.

Breakdown of hydrogen ortho-esters into carboxylic acid and alcohol products.

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