Beilstein Lecture notes

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BEILSTEIN: INFORMATION AND HOW TO USE
A. BACKGROUND
1. What is Beilstein?
Most comprehensive summary of information on organic chemicals anywhere, compiled in one place. A
critical review, all material is researched and documented at the Beilstein Institute includes ALL
known carbon compounds which have been described, obtained in a state of sufficient purity and
whose construction is known. All material is checked by scientists at the Beilstein Institute.
2. Why is it important?
This is the only resource that is organized by compound name. All information on each compound is listed
methodically and has been checked for accuracy. Every preparation and reaction is described and
cited, Once you find your compound in any Beilstein volume, you can find it anywhere in Beilstein
and have all the material on that compound at your fingertips.
3.Brief history
Begun in 1862 by Friedrich Konrad Beilstein who produced the first two editions himself, taught in Russia for
many years, 1st ed. took 20 yrs-1882, 2nd ed. 1886-1892, 3rd ed. 1892-1906, then issued by German
Chemical Society till after World War II, then Beilstein Institute. Purchased by Elsevier, 2007.
Now in 4th edition, with 5 supplemental sets (i.e. a total of 6 sets) 5th supplemental set is in English and is
being published, however, UML does not have any of it. Online version available as “CrossFire”, at
UMASS Amherst/MIT/Boston College but not UML. The complete database indexes over 6 million
compounds. Database covers 1828-1959 for reviewed (checked) data plus a "shortfile" of unchecked
data 1960-79.
4. Physical description of volumes, coverage
a.
b.
c.
d.
e.
Basic series (called Hauptwerke) covers period to 1909 and the spine label is green.
Supplementary series I (Erganzungwerke) covers 1910-1919 and the spine color is red.
Supplementary series II covers 1920-1929 and the spine label is white.
Supplementary series III covers 1930-49 and the spine label is blue.
Supplementary series III/IV covers 1930-1959 and has a blue/black label. Combined volumes were issued
beginning with vol. 17.
f. Supplementary series IV covers 1950-59 and the spine label is black.
g. Supplementary series V is now being issued
h. Indexes for suppl 1-4 are available Vol.1-8, 17-26 with green spine labels--filed at the end of all the
Beilsteins.
i. Dates not exactly accurate as they add info up to within 4 years of publishing date.
j. The volumes take up 4 ranges of shelves, and the older ones are somewhat delicate--please handle with care.
5. German words
Beilstein is all in German (5th ed. is English) but with the aid of a good dictionary (German-English), you
should be able to find needed information. Copies of the Beilstein dictionary are ON RESERVE.
This dictionary has the important words translated and specifically translates them within a chemical
context. This dictionary is also online.
a. German words to know: Seite=page; vgl=see, Saure=acid; Band=volume;
b. Many German nouns simply stick several words together. For example Dissoziationskonstante means
Dissociation constant. Malonsaure is Malonic Acid.
c. All German nouns are capitalized.
6. Abbreviations
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BEILSTEIN: INFORMATION AND HOW TO USE
a.Beilstein is notorious for its abbreviations. Abbreviation lists of commonly used terms are located on my
website. There is also an abbreviation list at the front of every volume. Keep abbreviations in
context. “B” at the beginning of the first paragraph means Bildungsweisen (preparation). “B” in a
literature reference means Berichte der Deutschen Chemische Gesellshaft, the premier German
chemistry journal (Which UML OWNS QD .D4) There are also abbreviations for common
Chemicals, such as A. for Athanol W for Wasser.
b. Journal abbreviations
Common abbreviations of Beilstein journals OWNED BY UML:
Am Soc=JACS (Journsl of the American Chemical Society)
B= Berichte
Soc= Journal of the Chemical Society of London
J O Chem=Journal of Organic chemistry
J Chem Ed=Journal of Chemical Education
A=Justus Leibig’s Annalen der Chemie
Org Syn=Organic Syntheses
B. ORGANIZATION
1. Front of each volume
a. list of full names of journals and other publications
used in vol., arranged alphabetically by abbreviation. 4th ed. 11 pages of journal references. Beilstein
journal abbreviations are Unique.
b. Tables of other abbreviations. used in Beilstein, one for physical properties, one for common
words/chemicals.
2. For each compound, entry gives:
a. structure, configuration, historical.
b. occurrence, formation, preparation the German word is Bildungweisen, abbreviated “B”
c. physical properties, color, physical constants.
d. chemical properties.
e. physiological action.
f. uses.
g. analytical data. (detection, examination, estimation)
h. ddition compounds & salts.
i. derivatives
1) Functional (replacing H with organic or inorganic atom or group)
2) Non-functioning group (replacing H by a non-functioning group ( -F, -Cl, -Br etc.)
3) Replacement group - replacing the "O" of a functioning group with S, Se, Te.
3. Indexes
a) In back of each volume (even volume parts in later supplements), a formula and a subject index are located.
It covers ONLY that volume unless noted on the spine (i.e. 3rd supp. have SOME
comprehensive indexes between vol 5-14).
b) There is a complete formula and subject index at the end of the second supplement (in German) References
in this index are to volume, page # (volume # are not repeated, so ref reads 5, 605, I, 285 II 395
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BEILSTEIN: INFORMATION AND HOW TO USE
etc.) which means vol 5 page 605, volume 5 of first supplement page 285 and volume 5 of
second supplement page 305.
c) In the comprehensive indexes, all the supplements are covered and the string looks like this:
Methan, Nitro74c, I 19 c, II 40 a, III 106 B, IV 100
letters mean position on the page and can be ignored
d) Later volumes include both System Number and page number on their spines BE CAREFUL S=Seite
(page) in German.
Spine example:
Band 2/3
S 1453-2662
System-Nr 163-194
Means: Volume 2, 3rd part. Pages 1453-2662, System numbers covered 163-194
e) Formula index = Formelregister; Subject index = Sachsregister.
f) Later volumes have formula indexes arranged by Hill notation
g) subject index arranged by compound name but in German
4. Citations
a. Every fact is cited.
b. Facts are organized into subject groups, similar facts are grouped together.
c. All facts are cited exactly, to the page (s) of the article on which the fact was mentioned.
d. Citations to the literature are brief. Repeated citations to the same paper are even briefer.
e. List of abbreviations for all journals is located in front of each volume. Beilstein does NOT use CASSI
abbreviations, they use their own abbreviations, which are much shorter, even one letter long in
some cases.
f. The following information is present: Last name of author/authors; abbreviated journal name, volume, page.
For patents: author/authors or company, country and number.
g. The following information is not present in early editions: year, page spans, first names or initials of
authors.
h. For preparations, a short phrase describes the prep, and all reactants are named.
5. Structural Formulas
a. In more recent supplements (3rd, 4th), all structural formulas are drawn clearly and labeled “Formel [Roman
numeral]. Drawings of each are placed as closely as possible to the entry but they may be located on
the page previous/following the entry you are consulting. In the first line of the entry, the number of
the structural formula will be given. Formulas are generalized, and use R, X for changing groups,
the entry will identify the exact molecule or group. When asked to draw a structural formula from
Beilstein, draw the formula and be sure and consult the entry to replace R, X, etc. with the molecule
or group that belongs there.
b. In older volumes, structural formulas are at the top of each entry, and are very tiny.
C. HIERARCHY
Beilstein system moved from simple to complex compounds
3 main divisions:
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BEILSTEIN: INFORMATION AND HOW TO USE
Acyclic compounds vol 1-4 System # 1-449
Isocyclic compounds vol 5-16 " 450-2358
These compounds are carbon rings only.
Heterocyclic compounds 17-27 " 2359-4720
These compounds have rings with one or more non-carbon atoms (i.e. beginning with O,then N ...)
Heterocyclic compounds are divided further according to type and # of heteroatoms
They follow the principle of latest systematic entry
If isocyclic compound has acyclic elements, it is with isocyclic
if heterocyclic compound has acyclic or isocyclic structural elements, it is with heterocyclic.
Compounds are always in the same relative place with regard to each other. If you can find your compound or a
related compound in a volume, it will be in the same volume in later supplements.
D. BACK REFERENCES
a. These appear in later supplements and are very important in assisting you to find earlier references.
b. This reference is located at the compound name--it is abbreviated in supplement 1, the only reference is "s.
226" which means look in the same volume, page 226 of the original work (this appears in () )
c. Supplement 2 has reference to H and EI
d. Supplement 3 has H, E I, E II.
e. Lack of a back reference means that the compound is being described in Beilstein for the first time.
f. System Numbers transfer from supplement to supplement e.g.system #523 will be the same set of compounds
no matter which supplement you use
g. Further guideline: H reference at top of even number pages. If you have a long article in the original volume
(i.e. it goes on for several pages) it is likely that in future volumes the material will be come even more extensive.
Therefore, so you don't have to look through pages of later supplements, just note the page number of the original
(i.e. 226) and look at the top of the page for the same number -- the information you want will be somewhere under
that page number. Easiest way to find a compound in the volume when you have the right volume in hand: Use the
molecular formula index in the back of the volume. Can also use Subject index, if you know the name of the
compound in German.
h. later editions these H references may go on for several pages, this is also a good way to verify that you are in
the right place, looking at the right compound, as they do change names from edition to edition.
E. OTHER REFERENCES INTO BEILSTEIN
a. Aldrich
refer mostly to the original Hauptwerke volumes, give a volume, page # only. Online version of Aldrich is
updating Beilstein Ref. to latest, am not sure if this is complete.
Beilstein numbers given in online Aldrich are only helpful for Crossfire, not for finding material in physical
volumes.
To find a newer reference if you only have the original reference
1. Use the index in the back of the volume. You must have the formula for your compound or the
German Name of the cpd.
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BEILSTEIN: INFORMATION AND HOW TO USE
2. Use the System Number and the H page number to get to the volume in the later supplelment, use
the index in that volume to find the cpd
3. Use another source to find the reference (CRC or HODOC)
4. Use a cumulated index, if one is available for your volume. The Cumulated Index will give ALL
back references.
5. Use a similar chemical that is listed in CRC to get to the right volume and section. This works for
cpds which are similar but have groups in different positions. EX: 1-chloro-2-methyl benzene would
be located quite near 2-chloro-3-methyl benzene.
b. CRC reference:
1.) OLD: are in the last column of the page. The reference is to volume and supplement number,
which is expressed as a superscript and page. ie. 73 805 is a ref to vol 7 of supplement 3, page 805.
NOTE: Because we have NO 5th supplement, you may need to use an older CRC to get a
reference to the 4th supplement.
2) NEW: 75th and forward: 4-01-00-00100 Supplement/volume/subvolume (5th only)/page number.
3) Beginning with 87th edition of CRC, no Beilstein references are given.
c.Handbook of Data on Organic Compounds: Includes Beilstein reference to latest supplement.
Reference exactly like CRC
d.
There are no Beilstein references in Merck OR DOC OR other online resources.
Marion Muskiewicz
Last updated 4/10/07
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