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Chemical Literature (Chem 184/284)

Assignment 1 Answer Key
Data Collections

Using the various reference books discussed in Lectures 4 and 5 or listed on the various Chemistry Guide pages, locate information about the subjects below. For each compound, you must give the CAS Registry Number. What other information you find is optional, but you must locate each compound or concept in at least three of the print sources I discussed in class, plus one Web source for the compounds. Describe clearly and thoroughly the type of information each source provides. DO NOT use indexes to the journal literature or give me journal references for this assignment.

Note that the name I give for the compound may not always be the name the compound is listed under in every source. In some cases, you may need to find the molecular formula or the structure of the compound in order to use a given source -- but remember that some sources will give you the keys you need to search other sources. Concepts have synonyms, too. Be creative!

Answers to these questions may be found at http://www.library.ucsb.edu/classes/chem184/184asn01a.html after the due date of the assignment.

Sample questions 1, 2 and 3 and answers 1 and 2 for this assignment using different compounds may be found at http://www.library.ucsb.edu/classes/chem184/184samq1.html, http://www.library.ucsb.edu/classes/chem184/184samq2.html and http://www.library.ucsb.edu/classes/chem184/184samq3.html and at http://www.library.ucsb.edu/classes/chem184/184sama1.html and http://www.library.ucsb.edu/classes/chem184/184sama2.html respectively if you want additional practice or some pointers on likely sources.

Compound 1: Zeise's salt
KPtCl₃(C₂H₄) CAS Registry #: 16405-35-9 (monohydrate)
12012-50-9 (anhydrous), 123334-22-5 (xH₂O)
12275-00-2 (anion)
Source (full name) Vol. # Page(s) Types of information given

Aldrich Catalog
(2000-01) N.A. p. 1423
#24,495-3 mol. formula, mol. wt. density,
melting pt. References for Safety, etc.
Dictionary of
Organometallic Compounds
2nd. ed. Vol. 3 p. 3015 Listed under the anion
mol. formula, mol. wt, references
Encyclopedia of
Inorganic Chemistry Vol. 8 p. 4363 formula, history
Comprehensive
Organometallic
Chemistry Vol.3; 6 p. 48; 489, 614, 633, 655, 663 structural data, C-C bond length; use as reagent; date of first synthesis, list of reviews; synthesis; IR bands; solution behavior
Comprehensive Organometallic
Chemistry II Vol 12 p. 602 Preparation
Inorganic Syntheses Vol. 14; 28 P. 90; 349 Detailed syntheses, safety precautions
Comprehensive Inorganic
Chemistry Vol. 4 819; 828; 839; 843; 846 discovery, synthesis; structure; IR bands; NMR peaks; reactions
Encyclopedia of Spectroscopy
and Spectrometry Vol. 2 p. 1034 Discussion of IR spectrum in structure detn.
Encyclopedia of Chemical Technology
4th. ed. Vol. 19 p. 396 brief mention, CAS Reg. number
Sax's Dangerous Properties
of Industrial Materials Vol. 3 p. 2884 mol. formula, mol. wt., CAS Reg. number, toxicity data w/reference.
Web Source URL Types of information given
ChemFinder www.chemfinder.com names, formula, links to other source
SDBS www.aist.go.jp/RIODB/SDBS/menu-e.html mol. formula, mol. wt. structure, H NMR spectrum, 2 IR spectra

Compound 1: Zeise's salt KPtCl₃(C₂H₄)	CAS Registry #: 16405-35-9 (monohydrate) 12012-50-9 (anhydrous), 123334-22-5 (xH₂O) 12275-00-2 (anion)
Source (full name)	Vol. #	Page(s)	Types of information given
Aldrich Catalog (2000-01)	N.A.	p. 1423 #24,495-3	mol. formula, mol. wt. density, melting pt. References for Safety, etc.
Dictionary of Organometallic Compounds 2nd. ed.	Vol. 3	p. 3015	Listed under the anion mol. formula, mol. wt, references
Encyclopedia of Inorganic Chemistry	Vol. 8	p. 4363	formula, history
Comprehensive Organometallic Chemistry	Vol.3; 6	p. 48; 489, 614, 633, 655, 663	structural data, C-C bond length; use as reagent; date of first synthesis, list of reviews; synthesis; IR bands; solution behavior
Comprehensive Organometallic Chemistry II	Vol 12	p. 602	Preparation
Inorganic Syntheses	Vol. 14; 28	P. 90; 349	Detailed syntheses, safety precautions
Comprehensive Inorganic Chemistry	Vol. 4	819; 828; 839; 843; 846	discovery, synthesis; structure; IR bands; NMR peaks; reactions
Encyclopedia of Spectroscopy and Spectrometry	Vol. 2	p. 1034	Discussion of IR spectrum in structure detn.
Encyclopedia of Chemical Technology 4th. ed.	Vol. 19	p. 396	brief mention, CAS Reg. number
Sax's Dangerous Properties of Industrial Materials	Vol. 3	p. 2884	mol. formula, mol. wt., CAS Reg. number, toxicity data w/reference.
Web Source	URL	Types of information given
ChemFinder	www.chemfinder.com	names, formula, links to other source
SDBS	www.aist.go.jp/RIODB/SDBS/menu-e.html	mol. formula, mol. wt. structure, H NMR spectrum, 2 IR spectra

Compound 2: Retin-A
Retinoic acid, all trans CAS Registry #: 302-79-4
Source (full name) Vol. # Page(s) Types of information given
Merck Index
12th ed. N.A. P. 1404
Merck #8323 mol. formula, mol. wt., preparation and use references
Aldrich Catalog
2000-2001 N.A. P. 1463
Aldrich #22,301-8 mol. wt., mp, references to Beilstein, Merck, Aldrich FT-NMR, FT-IR and safety handbooks. References for pharmaceutical effects.
Beilstein Handbook of
Organic Chemistry Vol. 9 P. 3118 (Suppl. 3)
P. 2387 (Suppl. 4) mol. form, structure, synthesis refs., UV ref.
mol. form. synthesis refs., IR ref., UV ref.
Dictionary of Organic Compounds
6th ed. Vol. 5 P. 5604
DOC #: R-0-00018 mol. formula, mol. wt., mp, LD50, references to preparation, characterization, pharmacology, etc.
Handbook of Physical Properties of Organic Compounds N.A. P. 302 CAS Reg. #, structure, mol. formula, mol. wt., mp, water solubility, log p, vapor pressure, Henry's Law const., hydroxyl radical reaction rate const.
Comprehensive Organic Functional
Group Transformations Vol. 1 P. 612 Use of sulfones (Julia synthesis) to synthesize.
Aldrich Library of
IR Spectra N.A. P.296E IR spectrum
Aldrich Library of
FT H and ¹³C NMR Vol. 1 P. 790A proton NMR, ¹³C NMR spectra
Sax's Dangerous Properties of Industrial Materials Vol. 3 P. 3505-3506
Sax #: VSK950 names, CAS Reg. #, mol. form., mol. wt., lots of toxicity data with references, safety profile.
Dictionary of Drugs Vol. 1 P. 1070
DD #: R-00033 names, structure, CAS Reg. #, mol. formula, mol. wt., mp, medicinal use, lots of references for synthesis, characterization, etc.
Web Source URL Types of information given
ChemFinder www.chemfinder.com names, structure, CAS Reg. #, mp, water solubility, links to other Web sources.
SDBS www.aist.go.jp/RIODB/SDBS/menu-e.html name, structure, mol. form., mol. wt., CAS Reg. #, IR spectrum

Compound 2: Retin-A Retinoic acid, all trans	CAS Registry #: 302-79-4
Source (full name)	Vol. #	Page(s)	Types of information given
Merck Index 12th ed.	N.A.	P. 1404 Merck #8323	mol. formula, mol. wt., preparation and use references
Aldrich Catalog 2000-2001	N.A.	P. 1463 Aldrich #22,301-8	mol. wt., mp, references to Beilstein, Merck, Aldrich FT-NMR, FT-IR and safety handbooks. References for pharmaceutical effects.
Beilstein Handbook of Organic Chemistry	Vol. 9	P. 3118 (Suppl. 3) P. 2387 (Suppl. 4)	mol. form, structure, synthesis refs., UV ref. mol. form. synthesis refs., IR ref., UV ref.
Dictionary of Organic Compounds 6th ed.	Vol. 5	P. 5604 DOC #: R-0-00018	mol. formula, mol. wt., mp, LD50, references to preparation, characterization, pharmacology, etc.
Handbook of Physical Properties of Organic Compounds	N.A.	P. 302	CAS Reg. #, structure, mol. formula, mol. wt., mp, water solubility, log p, vapor pressure, Henry's Law const., hydroxyl radical reaction rate const.
Comprehensive Organic Functional Group Transformations	Vol. 1	P. 612	Use of sulfones (Julia synthesis) to synthesize.
Aldrich Library of IR Spectra	N.A.	P.296E	IR spectrum
Aldrich Library of FT H and ¹³C NMR	Vol. 1	P. 790A	proton NMR, ¹³C NMR spectra
Sax's Dangerous Properties of Industrial Materials	Vol. 3	P. 3505-3506 Sax #: VSK950	names, CAS Reg. #, mol. form., mol. wt., lots of toxicity data with references, safety profile.
Dictionary of Drugs	Vol. 1	P. 1070 DD #: R-00033	names, structure, CAS Reg. #, mol. formula, mol. wt., mp, medicinal use, lots of references for synthesis, characterization, etc.
Web Source	URL	Types of information given
ChemFinder	www.chemfinder.com	names, structure, CAS Reg. #, mp, water solubility, links to other Web sources.
SDBS	www.aist.go.jp/RIODB/SDBS/menu-e.html	name, structure, mol. form., mol. wt., CAS Reg. #, IR spectrum

Concept 1: Baeyer-Villiger reaction
Source (full name) Vol. # Page(s) Types of information given
Merck Index
12th ed. N.A. P. ONR-4 reaction diagram, original paper ref., review article refs.
Kirk-Othmer's Encyclopedia
of Chemical Technology
4th ed. Vol. 9
Vol. 16
Vol. 18
Vol. 20 704,707,722
614
222
319 industiral uses
microbial catal.
urea peroxyhydrate as reagent
use in prostaglandin synthesis
Ullman's Encyclopedia
of Industrial Chemistry A8
A9
A18 39
431
269,282,284 use in making cresols
enzyme catal. of
industrial use, hydroperoxides and peroxy radicals in.
Organic Reactions Vol. 9
Vol. 43 P. 73-106
P. 251-798 (!) Both are comprehensive review articles, esp. the 2nd one.
Comprehensive Organic Synthesis Vol. 7 P. 671-686 overall review article
Comprehensive Organic Functional
Group Transformations Vol. 1,2,4,5,6 650;654;212;461,471;466 Examples of specific reaction cases.
Fieser and Fieser's Reagents
for Organic Synthesis Too numerous to mention Likewise Examples of various reagents have been successfully used for the B-V reaction.
Encyclopedia of Reagents
for Organic Synthesis Numerous references Likewise Uses of specific reagents for B-V reactions.
Comprehensive Heterocyclic Chemistry II Vol. 1 p.137 Lactam syntheses

Concept 1: Baeyer-Villiger reaction
Source (full name)	Vol. #	Page(s)	Types of information given
Merck Index 12th ed.	N.A.	P. ONR-4	reaction diagram, original paper ref., review article refs.
Kirk-Othmer's Encyclopedia of Chemical Technology 4th ed.	Vol. 9 Vol. 16 Vol. 18 Vol. 20	704,707,722 614 222 319	industiral uses microbial catal. urea peroxyhydrate as reagent use in prostaglandin synthesis
Ullman's Encyclopedia of Industrial Chemistry	A8 A9 A18	39 431 269,282,284	use in making cresols enzyme catal. of industrial use, hydroperoxides and peroxy radicals in.
Organic Reactions	Vol. 9 Vol. 43	P. 73-106 P. 251-798 (!)	Both are comprehensive review articles, esp. the 2nd one.
Comprehensive Organic Synthesis	Vol. 7	P. 671-686	overall review article
Comprehensive Organic Functional Group Transformations	Vol. 1,2,4,5,6	650;654;212;461,471;466	Examples of specific reaction cases.
Fieser and Fieser's Reagents for Organic Synthesis	Too numerous to mention	Likewise	Examples of various reagents have been successfully used for the B-V reaction.
Encyclopedia of Reagents for Organic Synthesis	Numerous references	Likewise	Uses of specific reagents for B-V reactions.
Comprehensive Heterocyclic Chemistry II	Vol. 1	p.137	Lactam syntheses

Concept 2: Applications of the polymerase chain reaction (PCR)
Source (full name) Vol. # Page(s) Types of information given
Kirk-Othmer Encyclopedia
of Chemical Technology
4th ed. 11
12
20 467
966
403 forensic chemistry
genetic engineering
protein engineering
Ullman's Encyclopedia
of Industrial Chemistry A18 23-24 Nucleic acids - amplification
Encyclopedia of
Analytical Science

1578-80
2062-64
4059-64 DNA profiling
antibody engineering
main article on methods
Encyclopedia of
Analytical Chemistry 5
6 4512-23
5159-73 forensic DNA
major chapter; history, "how-to", variations on PCR, applications.
Comprehensive Natural
Products Chemistry 4
6 211
651-660 synthesis of peptide antibiotics
cloning oligonucleotides

Concept 2: Applications of the polymerase chain reaction (PCR)
Source (full name)	Vol. #	Page(s)	Types of information given
Kirk-Othmer Encyclopedia of Chemical Technology 4th ed.	11 12 20	467 966 403	forensic chemistry genetic engineering protein engineering
Ullman's Encyclopedia of Industrial Chemistry	A18	23-24	Nucleic acids - amplification
Encyclopedia of Analytical Science		1578-80 2062-64 4059-64	DNA profiling antibody engineering main article on methods
Encyclopedia of Analytical Chemistry	5 6	4512-23 5159-73	forensic DNA major chapter; history, "how-to", variations on PCR, applications.
Comprehensive Natural Products Chemistry	4 6	211 651-660	synthesis of peptide antibiotics cloning oligonucleotides

Concept 3: Quantitative structure-activity relationships (QSAR)
Source (full name) Vol. # Page(s) Types of information given
Encyclopedia of
Computational Chemistry 4 2309-2319 Use of QSAR in drug design
Comprehensive
Medicinal
Chemistry 4 entire volume history, procedures, applications, etc.
Kirk-Othmer Encyclopedia
of Chemical Technology
4th ed. 5 339-343 computer methods in molecular modeling
Ullman's Encyclopedia
of Industrial Chemistry B1 12-94 - 12-96 computer models and approaches for drug design
This page created by Chuck Huber (huber@library.ucsb.edu).
Updated: 10/11/04 08:30:47

Chemical Literature (Chem 184/284)

Assignment 1 Answer Key Data Collections

Assignment 1 Answer Key
Data Collections