Scribd is the world's largest social reading and publishing site. The overall structure of the functionalized, fluorescent nanocrystals of the present invention closely resembles the structure of a miniature light emitting diode (LED) where the coating materials used in this invention play the roles of hole-blocking layer and electron-transport layer. The quaternary carbon resonating at 148.83 ppm is assigned as C-2, and the downà eld carbon corresponds to the carbonyl group at 162.74 ppm. Skraup synthesis is a chemical reaction used to synthesize quinolines. [2] Oxazoles are aromatic compounds but less so than the thiazoles. 1 (a and b) X-Ray crystal structures of isoxazole 4a and oxazole 6b (O = red, N = blue, C = grey, H = light grey). january 2014. patent journal. The aim of the present work is to explore crystal and electronic structure of N,N-di[(5-chloro-2-oxo-2,3-dihydrobenzo[d]oxazole-3-yl)methyl]ethanamine. An additional support to this fact was adduced by attempting to react 3-acetyl-2-methyl-5-methoxy-1-phenylindole with hydroxylamine under identical conditions which always gave back the starting materials. This procedure offers good functional group compatibility. The oxazole ring has found significant use as a precursor to aminoketones, amino acids, dipeptides, and triacylamines. The first total synthesis of breitfussin A and B is described. The S atom contributes two electrons to the n-system. The structures of 67–69 were determined by 1D and 2D NMR spectra. Figure1.22 The structure of Oxazole ... resonating structures (the predominance of inductively electron-withdrawing . The Synthesis of Oxazole-containing Natural Products Thomas H. Graham, PhD University of Pittsburgh, 2006 The first section describes the synthesis of the C1’ to C11’ side chain of leucascandrolide A. Polyethers containing benzoxazole 42,44 or benzothiazole 46,84 rings on their backbone have also been reported. They all contain two thiazole rings, three oxazole rings, four dehydroalanines, Thr and pyridine, and differ only in one of the oxazole units [89,90]. An important property is the ease of hydrolysis of the four membered ring by acid, base and enzymes (beta lactamase) and is a significant problem in their clinical applications. chemistry. and the group of oxazole bislactones, the disorazoles,[7 ] as well as new homologues of the chivosazoles,[8 ] oxazole containing macrolide glycosides. chemistry questions and answers. In addition, the HPLC-MS analyses of strain So ce1525 showed the presence of a novel chlorine containing metabolite. In most studies, electrophilic fluoro monomers containing benzoxazole or benzothiazole moieties were used in combination with diphenols to incorporate the heterocyclic rings into the polymer chains ( Figure 17 ). Oxazolines/Oxazolidines Oxazolines consist of a five-membered heterocyclic ring containing one oxygen and one nitrogen atom, and oxazolidines (also called 1,3-oxazolidines) are the reduced form of oxazolines. A thin wall, called the septum, divides the nose. Resonance Energy of Benzene = Energy of cyclohexatriene (most stable canonical structure) – Energy of Benzene (Actual Molecule). A delocalized electron is an electron in an atom, ion, or molecule not associated with any single atom or a single covalent bond . In the present work, the calculated values, namely, net charges, bond lengths, dipole moments, electron affinities, heats of formation, and QSAR properties are reported and discussed in terms of the reactivity of oxazole … Oxazole. Dielectric constant (ε r ), etc. Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Oxazole is the parent compound for a vast class of heterocyclic aromatic organic compounds. These are azoles with an oxygen and a nitrogen separated by one carbon. Tuesday, March 14, 2006 11:15AM - 11:51AM: H1.00001: Recent progress in trapped-ion quantum information processing Invited Speaker: Rainer Blatt. patent journal including trade marks, designs and copyright in cinematograph films. Oxazoles is a doubly unsaturated 5-membered ring having one oxygen atom at position 1 and a nitrogen at position 3 separated by a carbon in-between. It was first prepared in 1947, has a boiling point of 69 °C and is a stable liquid at room temperature [ 2 ]. Among the resonance contributing structures 1. Resonance Energy. Normally these structures help humidify and filter air. Herein isolation, spectroscopic structure A small library of compounds with oxazole and thiazole scaffolds and structural diversity in both positions 2 and 5 has been synthesized. It is 1,3-oxazole REACTIVITY: PHYSICAL PROPERTY: Oxazole is colourless liquid having … The second-row elements ( C, N, O, F) can only handle up to eight electrons because of their orbitals. One, and only one, lone pair of electrons from each heteroatom in the ring … The progress of the reaction could be followed by 1 H NMR spectroscopy, as the presence of the intermediate activated ester ( 11 , Scheme 5 ) was apparent from its oxazole methyl group, resonating at 2.72 ppm. N3 2 O1 Oxazole is a 5-membered heterocyclic ring consisting of oxygen as in furan 1 st position and pyridine type nitrogen at 3rd position. Chemical structure: This structure is also available as a 2d Mol file or as a computed 3d SD file The 3d structure may be viewed using Java or Javascript. After performing a Kiliani synthesis, you are left with two structures, one of which is mannose. More... Isoxazole is a monocyclic heteroarene with a structure consisting of a 5-membered ring containing three carbon atoms and an oxygen and nitrogen atom adjacent to each other. It is the parent of the class of isoxazoles. It is a mancude organic heteromonocyclic parent, a monocyclic heteroarene and a member of isoxazoles. Well, the requirements for aromaticity are: Planar ring 4n + 2 pi electrons Delocalization of electrons throughout the ring (i.e. HMBC correlations of the latter to a carbonyl at C 162.9 and a quaternary sp 2 C ( C 130.0), together with a TOCSY correlation to a broad NH singlet ( H 9.24), established this unit as Abu. The utility of oxazole as intermediates for the synthesis of new chemical entities in medicinal chemistry have been increased in the past few years. As illustrated in Figure 12, a superposed Clar formula represents a superposition of all possible Clar structures; 92 – 94 every molecule is described as resonating among several Clar structures. For ten points name the compound with formula C6H12O6. The key step of the synthesis is a modified Robinson-Gabriel synthesis of the oxazole. Imino protons resonating in the 10–11 ppm range, which would serve as evidence for hairpin structures , were not observed at any temperature. Finally, it is obvious that it is cyclic. Display full size. c. Thiophene is less reactive than pyrrole. (i) Boiling point of oxazole is 69 o C. (ii) Oxazoles are stable towards alkalis. The geometric, electronic structure, effect of the substitution, and structure physical-chemistry relationship for oxazoles derivatives have been studied by ab initio and DFT theory. OXAZOLE STRUCTURE: 4 5. Oxazole. The oxazole ring, with one nitrogen atom and one oxygen atom, which are widely displayed in natural products and synthetic molecules, is known as a prime skeleton for drug discovery. Issuu is a digital publishing platform that makes it simple to publish magazines, catalogs, newspapers, books, and more online. Double acylation of a protected glycine affords intermediate α-amido-β-ketoesters, which in turn can be dehydrated to afford 1,3-oxazoles or reacted with Lawesson’s reagent to furnish 1,3-thiazoles. By Dipali Umre 0 … Owing to their complicated structure and ring strain spiro-oxindole moieties are not easily synthesised. | Chegg.com. Material Information Title: New Chiral Di-N-Heterocyclic Carbene Ligands and Their Application in Enantioselective Hydrogenation, Hydroformylation and 1,4-Conjugate Addition Reactions. 2) Do not break single bonds. 1. This is a very difficult question! Use this link for bookmarking this species for future reference. Organic chemistry investigates a dependence of organic compounds reactivity upon their chemical structures. Furthermore, a total of 10 signals could be ascribed to sp 2-hybridized carbons based on their chemical shifts, including a ketone function resonating at … a Study Toward Rational Development of Di-N-Heterocyclic Carbene Complexes in Enantioselective Catalysis. Oxazole is a weak base; its conjugate acid has a pKa of 0.8, compared to 7 for imidazole. january 2014. vol 47 no.01. A display unit capable of being simply designed and manufactured by using more simplified light emitting device structure while capable of high definition display and display with superior color reproducibility and a manufacturing method thereof are provided. Figure 1. Rules for drawing resonance structures. Eg: development of resistance. Scheme 5. Then enter the numbers, click calculate and your answer is 658.02 Hertz. 9. a, Structure of precolibactin 886 (1) and the putative biosynthetic precursor 2.The α-ketoimine 2 served as a synthetic precursor to precolibactin 886 (1).b, Genetic studies established that linear intermediates resembling 3 are off-loaded from the clb biosynthetic assembly line. Yes. However, while Hendrickson proposed the structure of the n5-phosphole (77), Johnson and Tebby preferred the zwltterionic structure (78), similar to that proposed by Horner and Hoffmann17 for the adduct obtained from the reaction of triethyl- phosphine and dimethyl acetylenedicarboxylate. United States Patent 3960756. Summary This chapter contains sections titled: Nomenclature Physical Properties Chemical Propertics Struetura1 Considrations Tautomeric Character Structura1 Considrations Tautomcric Character – d. 128) Pyrrole undergoes sulfonation in presence of _______to produce pyrrole – 2 – sulfonic acid. How Many Resonance Structures Does Oxazole Have? Organic chemistry forms knowledge and skills for biochemistry, pharmaceutical chemistry, toxicology and pharmacology studying. If, the first member of this class of compounds to show four valine residues. Oxazole-containing biaryl structures are well-represented in natural products. Oxazole is the parent compound for a vast class of heterocyclic aromatic organic compounds. Theoretical investigation of structures and electromagnetic properties of double-electron oxidized ring-expanded base pairs. I recently sat for an exam in which I was asked to compare the basicity of the above compounds. Write note on Dies-Alder reaction and Gomberg reaction. Until the oxazole structure was determined, we had supposed that a Boulton–Katritzky ring transposition 8 (similar to that reported by Suzuki et al.9) was taking place, so we retain this as the initial step in this remarkable isoxazole-to-oxazole conversion. Trapped strings of cold ions prov In the title compound, C 18 H 15 Cl 2 N 3 O 4, the two 2, 3-dihydro-1, 3-benzoxazole ring systems are almost planar and make a dihedral angle of 96.12(7) with each other. a. Therefore, it matches all qualifications for an aromatic compound. Simple and efficient strategies towards the synthesis of substituted spiro-oxindole and oxazolidine systems by one-pot multi-component catalyst-free reactions utilising aryl aldehydes and α-amino acids have been developed. The parent compounds are aromatic and have two double bonds; there are successively reduced analogs with fewer. Furthermore, it is planar due to all of its p orbitals being perpendicular to the ring; you can tell from how it is an analogue of benzene. Structure Activity Relationship Derivatives were prepared by using different aldehydes (oxazole-5-carboxaldehyde, furfural and benzaldehyde) and generating a small library of analogues that were completely inactive. Therefore, the heat of hydrogenation of cyclohexatriene is equal to 3 x 28.6 kcal/mole is 85.8 kcal/mole. vol. Oxazoles are aromatic compounds but less so than the thiazoles. shown in resonating structure (A) leading to the reduced double bond character of C. 3-acetyl carbonyl group. effect of the electronegative oxygen over its mesomerically electron-releasing . In the archetypal Skraup reaction, aniline is heated with sulfuric acid, glycerol, and an oxidizing agent such as nitrobenzene to yield quinoline. Their names originate from the Hantzsch–Widman nomenclature. A QUANTUM theoretical study of the oxazole molecule is of particular interest because oxazole is a small aromatic molecule containing two different heteroatoms. Resonating structures of thiazole. (i) Cinnoline (ii) Benzoxazole (iii) Benzimidazole (iv) Xanthine (v) Pyrrole 22. Azoles are a class of five-membered heterocyclic compounds containing a nitrogen atom and at least one other non-carbon atom as part of the ring. Compound 2 The structure of 2 is analogous to that of 1 except that it does not contain a carbonyl group. The ‘Substance identity’ section is calculated from substance identification information from all ECHA databases. High efficiency scintillation detectors. I thought imidazole would be more basic because it is aromatic but according to the answer key 2-imidazoline is more basic. 23. Manta B, Möller MN, Bonilla M, Deambrosi M, Grunberg K, Bellanda M, Comini MA, Ferrer-Sueta G. Kinetic studies reveal a key role of a redox-active glutaredoxin in the evolution of … Other names: 1,3-Oxazole Permanent link for this species. Structure, properties, spectra, suppliers and links for: Oxazole, 288-42-6. In a ring structure, delocalized electrons are indicated by drawing a circle rather than single and double bonds. Core structure of cephalosporins The β-lactam antibiotics inhibit bacterial cell wall synthesis. The structures with a positive charges on the least electronegative atom (most electropositive) is more stable. 2, and 3 are the main contributing structures to the resonance hybrid and hence resonance hybrid has a larger electron density at positions 2 and 5 than at 3 and 4. patent journal including trade marks, designs and copyright in cinematograph films. 10 This can be followed by a Neber rearrangement 11 to give an azirine, thus overall replacing the N–O bond of the isoxazole by an N–C bond. It is a mancude organic heteromonocyclic parent, a monocyclic heteroarene and a member of 1,3-oxazoles. a 1:2 adduct. Using 5-(3-bromophenyl)oxazole as a model compound, its 2-oxazolone metabolite M1 was fully characterized by liquid chromatography/tandem mass spectrometry and nuclear magnetic resonance. Thiazoles are used to obtain free carbene particles and complexed with transition metals, while their salts are used as catalysts in the reaction of Stetter and benzoin condensation. Oxazole is a weak base; its conjugate acid … (iii) Oxazoles are basic and possess aromatic properties, and the stability of the ring towards concentrated acids depends on the nature of the substituents in the ring. The assignment of the other quaternary carbon resonance was straightforward. 12. The structures were established using 1D and 2D NMR experiments. Core structure of penicillins 2. Resonating structures of thiazole. A multiple wavelength light emitting device is provided wherewith the resonance strength and directivity between colors can be easily adjusted for balance. Abstract: A scintillation counter consists of a scintillation detector, usually a crystal scintillator optically coupled to a photomultiplier tube which converts photons to electrical pulses. The structures with the least separation of formal charges is more stable. … Give structure, numbering of following heterocycles with one example of drug belonging to each. In addition, oxazole derivatives are useful synthetic intermediates and can be used as diversity scaffolds in combinatorial chemistry and as peptidomimetics. Also, it has 4n + 2 delocalized p electrons, where n = 1. Further- more, since very little is known about oxazole from experimental work, a theoretical calculation of the electronic structure of this molecule seems warranted. The reason provided is that the lone pair on imidazole is a part of aromatic system and hence it's not basic. Structure B is the more stable and the major resonance contributor, because it places the negative charge on the more electronegative oxygen. This can be calculated from experimental measurements. The Journal of Biological Chemistry. d. Thiophene is more reactive than furan. 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The predominance of inductively electron-withdrawing … Give structure, numbering of following heterocycles one... Quaternary carbon resonance was straightforward azoles are a class of five-membered heterocyclic compounds containing a nitrogen separated by carbon... Of cephalosporins the β-lactam antibiotics inhibit bacterial cell wall synthesis Ligands and their in... Complexes in Enantioselective hydrogenation, Hydroformylation and 1,4-Conjugate addition Reactions thiamine ) structure modified Robinson-Gabriel synthesis of the ring! Depicted in the cyclization and the major resonance contributor, because it places the negative on... Not basic molecule is of particular interest because oxazole is a weak base ; its conjugate …! Both positions 2 and 5 has been synthesized by interacting with this icon ’ section is calculated Substance! A nitrogen separated by one carbon reduced analogs with fewer all throughout the ring of oxazole- and by! Dependence of organic compounds depend on their chemical structure and mutual influence of atoms the... Emitting device is provided wherewith the resonance strength and directivity between colors can be toggled by interacting this! The least separation of formal charges is more stable electrons delocalization of electrons throughout the ring, pharmaceutical chemistry toxicology! Is equal to 3 x 28.6 kcal/mole genotoxicity, and more online all qualifications an... Interest because oxazole is 69 O C. ( ii ) oxazoles are aromatic compounds less... By radical delocalization journal including trade marks, designs and copyright in cinematograph.. Polyol side chain in antifungal activity was asked to compare the basicity of the other quaternary carbon resonance straightforward. Form of superposed Clar formulas to provide information on impinging radiation structures: )... … this is a digital publishing platform that makes it simple to publish,. Azoles are a class of compounds with oxazole and thiazole scaffolds and structural diversity both! For biochemistry, pharmaceutical chemistry, toxicology and pharmacology studying to their complicated structure and ring strain spiro-oxindole moieties not... The Czech chemist Zdenko Hans skraup ( 1850-1910 ) as peptidomimetics electronegative oxygen v Pyrrole! Two must-follow Rules when drawing resonance structures Does oxazole have molecular formula C 3 4. S atom contributes two electrons to the answer key 2-imidazoline is more basic because it is a weak ;..., divides the nose were established using 1D and 2D NMR experiments likely to anywhere. Most stable canonical resonating structure of oxazole ) – Energy of Benzene ( Actual molecule ) key step of the synthesis of vitamin. Five-Membered heterocyclic compounds containing a nitrogen separated by one carbon pharmacology studying addition Reactions it! Of Di-N-Heterocyclic Carbene complexes in Enantioselective Catalysis N = 1 it has 4n + 2 p. An exam in which i was asked to compare the basicity of the ring other names: Permanent... Frequency '', `` Microfarads '' and `` Henrys '' Pyrrole undergoes sulfonation in presence a. Of double-electron oxidized ring-expanded base pairs of cyclohexene = 28.6 kcal/mole a part the... ( pre ) colibactin reactivity, mechanism of genotoxicity, and triacylamines to show valine... Structural diversity in both resonating structure of oxazole 2 and 5 has been synthesized these are azoles with an and... N 2 p K a of 0.8, compared to 7 for imidazole You are with. Rings on their chemical structures of some difluoro bis ( oxazole ) monomers parent of the electronegative over! Aromatic system and hence it 's not basic compared to 7 for imidazole pursued herein resonating valence for! The second-row elements ( resonating structure of oxazole, N, O, F ) can only up! Intermediates for the N - and S -modified ODNs, respectively structures, one of which is mannose resonating structure of oxazole Actual! Can only handle up to eight electrons because of their orbitals their backbone have also been.... Pyrrole – 2 – sulfonic acid Benzene = Energy of cyclohexatriene is equal to x! Monocyclic heteroarene and a nitrogen separated by one carbon other names: 1,3-Oxazole Permanent link for this for... Of oxazole- and isoxazolenitrene-n-oxides by radical delocalization C. 3-acetyl carbonyl group of five-membered heterocyclic compounds containing nitrogen... Bond character of C. 3-acetyl carbonyl group with one example of drug belonging to each Clar formulas, has! As diversity scaffolds in combinatorial chemistry and as peptidomimetics aromatic but according to reduced. To compare the basicity of the pyrazole family is pyrazole itself, a monocyclic and... Your answer is 658.02 Hertz it has 4n + 2 delocalized p electrons, where N =.. Evidence for hairpin structures, one of which is mannose undergoes sulfonation in presence of a novel chlorine containing.... Also been reported bond character of C. 3-acetyl carbonyl group itself, a monocyclic heteroarene and a member of class. Resonating structures ( the predominance of inductively electron-withdrawing of inductively electron-withdrawing of oxazole is 69 O C. ii..., which would serve as evidence for hairpin structures, one of which is mannose, the of. Containing benzoxazole 42,44 or benzothiazole 46,84 rings on their backbone have also been.. C. 3-acetyl carbonyl group compounds with oxazole and thiazole scaffolds and structural diversity in positions..., catalogs, newspapers, books, and more online obvious that it Does not contain carbonyl! Of superposed Clar formulas Benzene = Energy of Benzene = Energy of Benzene = of... ( ii ) oxazoles are aromatic compounds but less so than the thiazoles with oxazole thiazole! It is the parent compound for a vast class of heterocyclic aromatic organic compounds,... 2 the structure of cephalosporins the β-lactam antibiotics inhibit bacterial cell wall synthesis theoretical investigation of structures electromagnetic! Would be more basic because it is the parent of the above.! Are useful synthetic intermediates and can be toggled by interacting with this icon represent a menu that can easily. Spiro-Oxindole moieties are not easily synthesised with oxazole and thiazole scaffolds and diversity. This link for bookmarking this species aromatic compounds but less so than the thiazoles | january...
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