Fluorescent detection of hydrazines via fluorescamine and isomeric phthalaldehydes

Weeks, R. W.; Yasuda, Stanley K.; Dean, Brenda

doi:10.1021/ac60365a031

Cited by 26 publications

(7 citation statements)

References 19 publications

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“…Reaction of OPA with hydrazine yields a fluorescent species at pH 4−6 . On the basis of fluorescence of the final product, a ftalazine derivative, and comparison with reactions of analogous 1,2-dicarboxaldehydes derived from naphthalene and anthracene, the following reactions, eqs 6−9, have been proposed …”

Section: 4 Reactions With Hydrazinementioning

confidence: 99%

Reactions of Orthophthalaldehyde with Nucleophiles

Zuman

2004

Chem. Rev.

127

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Contents 1. Introduction 3217 2. Addition of a Single Nucleophile to OPA 3218 2.1. Addition of Water and Hydroxide Ions 3218 2.2. Addition of Alcohols 3219 2.3. Addition of Ammonia and Primary Amines 3219 2.4. Reactions with Hydrazine 3219 2.5. Reactions with Amino Acids 3220 2.6. Reactions with Amides, Urea, and Thiourea 3221 2.7. Reactions with Carbanions 3221 2.8. Reactions with Thiols and Other Sulfur Compounds3222 3. Reactions in the Presence of Two Nucleophiles 3223 3.1. Reagents 3224 3.1.1. Role of the Carbonyl Compound 3224 3.1.2. Stability of the Mixed Reagent 3224 3.1.3. Structure of the Thiol 3224 3.1.4. Structures of Amino Acids and Amines 3225 3.2. Sequence of Addition 3225 3.3. Reaction Medium 3225 3.4. Kinetics of the Formation of the Primary Product 3227 3.5. Consecutive Reactions of the Isoindole DerivativesStability of the Product of the Analytical Reaction 3228 3.6. Proposed Reaction Schemes 3232 3.6.1. Scheme Proposed by Simmons and Johnson 3232 3.6.2. Scheme Proposed by Wong, Sternson, and Schowen 3232 3.6.3. Scheme Proposed by Sternson, Stobaugh, and Repta 3233 3.6.4. Scheme Proposed by Gladilovich, Kartsova, and Zakharova 3233 3.6.5. Scheme of the Degradation of the Derivative of 2-Mercaptoethanol 3233 3.6.6.Scheme for Autoxidation of the Isoindole 3234 3.6.7. Conclusions Regarding Reaction Scheme 3234 3.7. Techniques Used 3234 3.8. Other Uses of the Reagent Formed in Reaction of OPA with Thiols 3235 3.9. Reagents Prepared by Reaction of Orthophthalaldehyde with Nucleophiles Other than Thiols 3235 3.10. Some Biochemical Applications 3236 4. Conclusions 3237 5. Acknowledgment 3237 6. References 3237

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Section: 4 Reactions With Hydrazinementioning

confidence: 99%

Reactions of Orthophthalaldehyde with Nucleophiles

Zuman

2004

Chem. Rev.

127

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“…In each reaction based upon amino functionality, it was important to note the potential for "false positive" results. Interferences for either the fluorogenic or chromogenic derivatives may be caused by other primary amines (3,9,10,11), amino acids (9,12), isocyanates (21) (either directly or by hydrolysis to amines ( 22)), indoles (23, 24), hydrazines (25), hydrogen peroxide (26), tryptophan (27), pyrroles (23), or phenols (28, 29) which coexist with the primary analytes. Species which are, of themselves, normally capable of fluorescence without derivatization may, likewise, cause false positives.…”

Section: Resultsmentioning

confidence: 99%

Detection limits of chemical spot tests toward certain carcinogens on metal, painted, and concrete surfaces

Weeks¹,

Dean²,

Yasuda³

1976

Anal. Chem.

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“…Picomole quantities of amines, amino acids, and proteins have been detected by reaction with o-phthalaldehyde and thiols (Davis, 1979;Simons, 1976;Roth, 1971;Weeks, 1976 Since fluorescent spot testing of hydrazines with fluorescamine and isomeric phthalaldehydes has been reported (Weeks, 1976), it appeared that this technique would be applicable to the low-level detection of MMH. However, preparation of the o-phthalaldehyde derivative by the method of Davis (1979) and analysis by HPLC gave inconclusive results as to the applicability of this method for low-level MMH detection.…”

Section: O-phthalaldehyde Derivative Studiesmentioning

confidence: 99%