Nucleophilic micelles. II. Effect on the rate of solvolysis of neutral, positively, and negatively charged esters of varied chain length when incorporated into nonfunctional and functional micelles of neutral, positive, and negative charge

Bruice, Thomas C.; Katzhendler, Jehoshua; Fedor, Leo R.

doi:10.1021/ja01007a040

Cited by 58 publications

(14 citation statements)

References 4 publications

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“…Compounds 2b-g were prepared by published procedures and had mp in satisfactory agreement with the literature values (35)(36)(37)(38). 2h was prepared by reaction of 2d with CH2N2 in diethyl ether, and recrystallized from petroleum ether: mp 72-73.5 "C. Anal.…”

Section: Substratessupporting

confidence: 60%

A catalyst for ester hydrolysis showing electrostatic and hydrophobic binding properties

Guthrie¹,

Ueda²

1976

Can. J. Chem.

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. Can. J. Chem. 54, 2745Chem. 54, (1976. The steroid 17p-(4-imidazoly1)-5~~-androstane-3p,l lp-diamine, l a , R = H , acts as a catalyst for the hydrolysis of aryl esters. For a series of aryl acetates, 2a-/I, at 1 M ionic strength, log kz for l a catalyzed hydrolysis is linearly related to log kz for imidazole catalyzed hydrolysis, with only 2d, 4-acetoxy-3-nitrobenzoate, deviating: at zero ionic strength, all anionic substrates show positive deviations, and a cationic substrate shows a negative deviation. This is interpreted in terms of a stringent geometrical requirement for strong electrostatic catalysis. With favorable geometry, a 1 :1 electrostatic attraction can lead to a 15 fold rate enhancement ( r = 0). For a series of arylpropionate esters 3a-c, rate constants for l a catalyzed hydrolysis show a small but progressive increase with increasing size of the aryl group: after correcting for substrate reactivity and electrostatic interactions, this hydrophobic effect is independent of the leaving group. l b (R = isopropyl) was prepared to determine the rate of reaction at N-3 of the steroidal imidazole ring: this is the more hindered nitrogen but also the more suitable for hydrophobic binding. l b was markedly less reactive than l a , but showed larger hydrophobic effects. Detailed analysis suggests that the potential hydrophobic rate enhancement for the interaction of a phenanthryl group with the lower surface of a steroid is about 160-fold. This study provides guidelines for the design of enzyme models of greater catalytic efficiency.

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Section: Substratessupporting

confidence: 60%

A catalyst for ester hydrolysis showing electrostatic and hydrophobic binding properties

Guthrie¹,

Ueda²

1976

Can. J. Chem.

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“…(1) represents the ionisation of peracid in the bulk water phase and the mixed acid dissociation constant, K a , is defined in eqn. (7), where {H ϩ } w is the hydrogen ion activity measured…”

Section: Resultsmentioning

confidence: 99%

“…Bruice has discussed orientational effects in similar terms for the reaction of hydrophobic 3-nitro-4-hydroxybenzenesulfonate esters with micelles of surfactants with reactive amino groups. 7 The effect of SDS on the reaction of hydrogen peroxide and n-nonanoyloxybenzenesulfonate is shown in Fig. 3.…”

Section: Discussionmentioning

confidence: 99%

Micellar kinetics of acyl transfer from n-nonanoyloxybenzenesulfonate and phenyl nonanoate bleach activators to hydrogen peroxide and pernonanoic acid: effect of charge on the surfactant and activator

Davies¹,

Foggo²,

Paradis³

1998

J. Chem. Soc., Perkin Trans. 2

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“…decreased in the presence of surfactants. 87 Substituents on the phenyl ring were also found to inuence the rate.…”

Section: Current Activatorsmentioning

confidence: 98%

Bleaching systems in domestic laundry detergents: a review

2015

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Laundry detergent is an indispensable commodity which is used by consumers worldwide. The global market for laundry detergents is in the region of $60.9 billion (2012, based on retail value), of which $11.7 billion comes from Western Europe. Non-chlorine bleach was incorporated in a detergent for the first time just over a century ago and it remains an important component of detergents, particularly powder detergents. Detergent development is mainly carried out in industrial laboratories and, as a result, relatively few papers have been published in this area. The aim of this review is to compile this information, along with that contained in the patent literature and other sources, to give future researchers a more comprehensive overview of this important topic. Specifically, oxygen-based bleaching systems have been examined, with focus on their development through the years. Current research targets as described by the available literature are also discussed, such as the development of better bleaching species, alternative bleach systems, and steps to incorporate a bleaching system in liquid laundry detergents (a key development which continues to elude researchers).

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Nucleophilic micelles. II. Effect on the rate of solvolysis of neutral, positively, and negatively charged esters of varied chain length when incorporated into nonfunctional and functional micelles of neutral, positive, and negative charge

Cited by 58 publications

References 4 publications

A catalyst for ester hydrolysis showing electrostatic and hydrophobic binding properties

A catalyst for ester hydrolysis showing electrostatic and hydrophobic binding properties

Micellar kinetics of acyl transfer from n-nonanoyloxybenzenesulfonate and phenyl nonanoate bleach activators to hydrogen peroxide and pernonanoic acid: effect of charge on the surfactant and activator

Bleaching systems in domestic laundry detergents: a review

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