A-Naphthaleneacetic acid

Acetonitrile is used in the chemical industry as an intermediary in the synthesis of several chemicals and products such as acetophene, thiamine, acetamidine, and a-naphthaleneacetic acid,... 

The major natural auxin is indole-3-acetic acid (lAA) [42]. A number of related compounds exist in plants, including indolebutyric acid and indoleacetonitrile (Fig. la). These related compounds are active primarily when first converted to lAA [42]. In addition, there are a series of LAA conjugates with sugars and amino acids [43]. Some of these may be detoxification products, but others may be reservoirs of releasable lAA, especially in seeds. Phenylacetic acid (Fig. la) has auxin activity, and exists in sizable amounts in a few plants such as tobacco [42], but it is unclear that this compound actually moves from one part of a plant to another. In addition to the natural auxins, a whole host of synthetic auxins are known. The most widely used are a-naphthaleneacetic acid (NAA) and 2,4-dichlorophenoxyacetic acid (2,4-D) (Fig. la). 

The degradation, by decarboxylation, of a-naphthaleneacetic acid has been shown to be wavelength dependent. Short wavelengths are the more destructive and the decarboxylation follows pseudo-first order kinetics. The photodegradation of 2,4-dihydroxybenzoic acid in water catalysed by titanium dioxide has been reported in some detail. ... 

Irradiation of 2-[N-(pentafluorophenyI)amino]-3-phenylcyclopropenone promotes decarbonylation to give N-(pentafluorophenyl)phenylethynamine and 2-phenyl-3-[N-(pentafluorophenyl)amino]acrylic acid by a process for which there is no known precedent,and the photoextrusion of carbon monoxide from l,3-bis(ethylenedioxy)indan-2-one has been used as the first step in a new synthesis of 1,2-dioxobenzocyclobutene. This represents an unusual example of the decarbonylation of a five-membered cyclic ketone in the preparation of a highly strained and functionalised cyclobutane derivative. The photolysis of a-naphthaleneacetic acid in aqueous solution proceeds by decarboxylation and oxidation of the aromatic ring, and has been carried out at a variety of different wavelengths. The primary step occurs by pseudo-first order kinetics and the optimum photolysis rate has been observed using Ti02 as photocatalyst. Within the cavity of P-cyclodextrin, naproxene (129) has been photodecarboxylated to... 

The acidic pesticides, except for picloram and the phenols, are considered nonvolatile, and losses of the chemicals from aqueous and soil systems are usually insignificant. Anderson et ah (184) found no loss of 2,4-D acid and only a small loss of a-naphthaleneacetic acid when the compounds were applied to glass slides. Schliebe et ah (156) found no loss because of volatizing when chloramben was applied to seven different soils. The vapor pressures of most acid pesticides are low or negligible (Table IV). 

Naphthaleneacetic acid a-Naphthaleneacetic acid. See 1-Naphthylacetic acid... 

The chemical synthesis of lAA was first reported by Johnson and Crosby [2]. Many lAA-related compounds have been synthesized, and a-naphthaleneacetic acid possesses almost the same activity as lAA. Because lAA can be produced inexpensively, it is used in agricultural practice. On the other hand, (2,4-dichlorophenoxy) acetic acid (2,4-D, 2,4-Cl2-C6H30-CH2COOH) possesses strong root elongation activity. Since overstimulation of such activity blights plants, it is used as a herbicide. 

Veen H (1969) Auxin transport, auxin metabolism and ageing. Acta Bot Neerl 18 447-454 Veen H (1972) Relationship between transport and metabolism of a-naphthaleneacetic acid and a-decalylacetic acid in segments of Coleus, Planta 103 35-44 Veen H (1975) Non-polar translocation of abscisic acid in petiole segments of Coleus. Acta Bot Neerl 24 54-62... 

Media B5 = Gamborg et al. (1968) MS = Murashige and Skoog (1962) W = White (1954). Growth hormones 2,4-D = 2,4-dichlorophenoxyacetic acid NAA = a-naphthaleneacetic acid IBA = indolylbutyric acid KIN = kinetin ZEA = zeatin BA = 6-benzyladenine 2iP = 2-isopen-tenyladenine... 

AIkyl-Ai,A/-diaLkyl-l-naphthalenecarboxamides are useful herbicides (86) and the 2,2-dimeth5lhydra2ide of 1-naphthalenecarboxyhc acid has been patented as a plant growth regulator (87). 2-Propynyl-2-naphthalenecarboxylate [53548-27-9] and similar esters are insecticides (88). 1-Naphthaleneacetic acid, the plant growth regulator, has been prepared from naphthalene, concentrated HCl, and paraformaldehyde without isolation of intermediate 1-chloromethylnaphthalene or l-naphthaleneacetonitnle (89). 

Hydroxy-1-naphthaleneacetic acid [10441-45-9] M 202.2, pK )-4.2, pKej,(2) -8.3. Treated with activated charcoal and crystd from EtOH/water (1 9, v/v). Dried under vacuum, over silica gel, in the dark. Stored in the dark at -20° [Gafni, Modlin and Brand J Phys Chem 80 898 1976. Forms a lactone (m 107°) readily. 

Chemical Name (+)-6-methoxy-a-methyl-2-naphthaleneacetic acid Common Name d-2-(6-methoxy-2-naphthyl)propionic acid Structural Formula ... 

CN (S)-6-methoxy-a-methyl-2-naphthaleneacetic acid sodium salt... 

Naphthaleneacetic acid, a-fluoro-, ethyl ester [24021-14-5], 57, 73 1,4-Naphthalenedione [130-15-4], 56, 70... 

With the larger racemic cr-hydroxy-l-naphthaleneacetic acid too, extraction takes place in the presence of 1309] and the appropriate cations but enantiomeric differentiation is not observed. These results were confirmed in transport experiments in which the alkali mandelate is carried through a liquid membrane of [309] dissolved in chloroform. Lehn et al. (1978) explain these observations in terms of an ion pair included in the cavity of the crown ether. The reversal of chiral recognitions between potassium and cesium mandelate of 25% indicates that the structures of the two complexes are different. 

Rheum palmatum Callus culture was induced from petiole of plant cultivated in vivo on the Murashige-Skoog (MS) medium (Murashige and Skoog, 1962) gelled by agar (8g/l), supplemented with naphthaleneacetic acid (NAA) (10 mg/1) and casein hydrolyzate (2 g/1). Callus subcultured every 4 weeks was transferred into the liquid medium and filtered through a sieve (mesh 3 mm). 

A number of drugs have been successfully separated using MIPs. Naproxen , (S)-6-methoxy-a-methyl-2-naphthaleneacetic acid, is a nonsteroidal anti-inflammatory drug (NSAID) that is administered as the S enantiomer. Naproxen (structure 16.20) will be used to illustrate the MIP sequence. Naproxen has both polar and nonpolar domains. It also has a fused-ring aromatic site. 

Naphthaleneacetic acid A /J-Chlorophenylphthalamic acid 2,3,5-Triiodobenzoic acid 8, 12-14)... 

X-Ray diffraction techniques were used to help in the study of a QSAR of artemisinin 1 <2002JME292>, as well as in the determination of the structure of the artemisinin intermediate a,4-dimethyl-decahydro-7-oxo-l-naphthaleneacetic acid 7, where the cyclohexane ring assumes a chair conformation and the cyclohexanone ring a distorted one <1995JCX473>. 

Ueno et al. found that two naphthalene derivatives can be included in the large cavity of y-CD [29], This result was obtained by observing enhanced excimer emission in the solution of y-CD and 2-naphthaleneacetic acid. On this basis, y-CD with one appending naphthalene moiety was shown to form a complex in... 

Chemical Name a-Methyl-l-naphthaleneacetic acid l,4-piperazinediyldi-2,l-ethanediyl ester... 

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