ORGANIC CHEMISTRY RESOURCES

About 12 years ago, an organic chemistry directory http://murov.info/orgchem.htm was launched.  The site was intended to assist organic chemists and students with searches for information.  Because of the explosion of chemistry web sites, maintenance of the site has become challenging.  Instead, this new site has been developed that is more selective and hopefully easier to use.  Some of the information comes from my online organic chemistry lab book:   http://murov.info/orglab.htm.  Please send comments and suggestions to:
Steve Murov, murovs@yosemite.edu       

Four of the giants of organic chemistry:                                                                                                                                         R. B. Woodward                         Fredrich Wöhler

CONTENTS

I.  Properties

A.  Solvents

B.  Compounds

C.  Search for Compounds from Properties

II.  IR

A.  Spectra Collections

B.  Group Frequencies

C.  Analysis Approach

III.  NMR

A.  Spectra Collections

B.  Chemical Shifts

IV.  MASS SPECTROMETRY

A.  Spectra Collections

B.  Fragments Lost
C.  Fragments

V.  UV-Vis

A.  Spectra Collections 

VI.  REACTIONS, SYNTHESIS                                                                                                                                          Percy Julian

A.  Resources

B.  Reaction-Map

VII.  LABORATORY EXPERIMENTS

A.  Techniques

B.  Distillations

1.  Distillation Plates

2.  Boiling Points Under Reduced Pressure

C.  Safety

D.  Experiments

VIII.  HISTORY of ORGANIC CHEMISTRY
           A.  Timeline
           B.  History

IX.  PERIODIC TABLES

A.  Samples   

B.  Collections

C.  Element Properties                                                                                                                                                           Mary Fieser

D.  Periodic Trends
E.  Directories

F.  Timeline

X. ELECTRONEGATIVITY VALUES

XI.  HAMMETT PARAMETERS

XII.  pH INDICATORS, pKa VALUES
        A.  pH Indicators
        B.  pKa Values

XIII.  ORGANIC CHEMISTRY DIRECTORIES   

XIV.  MOLECULAR MODELS (drawing programs)

XV.  EDUCATION

A.  Online Textbooks

B.  Journals

 

I.  PROPERTIES

A.  Solvents
        http://murov.info/orgsolvents.htm     http://murov.info/orgsolvsort.htm

B.  Properties
       Murov - http://murov.info/orgcmpds.htm
       WolframAlpha - http://www.wolframalpha.com/
       Chemical Book - http://www.chemicalbook.com/
       Chemidplus - https://chem.nlm.nih.gov/chemidplus/    https://chem.nlm.nih.gov/chemidplus/chemidlite.jsp
       Stenutz - http://www.stenutz.eu/chem/search.php
       ChemBK - https://www.chembk.com/en
       Knovel Critical Tables (If using Explorer, it must be newest version)
                  (21824 compounds in sortable tables) - login required  -
                  initial registration or login:  https://app.knovel.com/web/register.v  
                  already registered login:  https://app.knovel.com/web/login.v ,
                  click on or copy and paste:   https://app.knovel.com/web/view/itable/show.v/rcid:kpKCTE000X/cid:kt002VLXT1/viewerType:itble/
                        To filter the listing, click on the triangle following the desirred parameter, select filter and then enter the limits of the desired parameter (<, > or =) and hit enter.
                        (7274 Compounds in sortable tables) - https://app.knovel.com/web/view/itable/show.v/rcid:kpKS000009/cid:kt00395F16/viewerType:itble/
       ChemSynthesis - https://www.chemsynthesis.com/
       PubChem - https://pubchem.ncbi.nlm.nih.gov/
       Vermont Safety Information Resources, Inc. MSDS - http://hazard.com/msds/ 

C.  Search for Compounds from Properties
         Aldrich - http://www.sigmaaldrich.com/catalog/search/substructure/OldSubstructureSearchPage
                    accepts - formula, structure, molecular mass, mp, bp, density
        ChemExper Chem Directory - http://www.chemexper.com/advanced_search.shtml
                    accepts - formula, structure, molecular mass, bp, mp, refractive index, density, ir, nmr    
        ChemNet Data Base   http://poc.chemnetbase.com/faces/chemical/ChemicalSearch.xhtml   
                    accepts formula, melting point, boiling point
        Chemspider - http://www.chemspider.com/FullSearch.aspx
                    accepts - formula, molecular mass 
        Melting point and molecular mass search:  https://chem.nlm.nih.gov/chemidplus/
                    accepts -  formula, mp, bp
        Murov - http://murov.info/orgcmpds.htm
                    search by molecular mass, bp, mp, density, refractiive index
       Organic Chemistry Data Base - http://www.colby.edu/chemistry/cmp/cmp.html    
                    accepts - formula, molecular mass, mp, bp, density, refractive index, ir, ms
       NIMC site - http://sdbs.db.aist.go.jp/sdbs/cgi-bin/cre_index.cgi?lang=eng
                    accepts - formula, molecular mass, ir, nmr, ms 
       Polymers - http://www.matweb.com/search/PropertySearch.aspx
       Knovel Critical Tables (If using Explorer, it must be newest version)
                  (21824 compounds in sortable tables) - login required  -
                  initial registration or login:  https://app.knovel.com/web/register.v  
                  already registered login:  https://app.knovel.com/web/login.v ,
                  click on or copy and paste:   https://app.knovel.com/web/view/itable/show.v/rcid:kpKCTE000X/cid:kt002VLXT1/viewerType:itble/
                        To filter the listing, click on the triangle following the desirred parameter, select filter and then enter the limits of the desired parameter (<, > or =) and hit enter.
                        (7274 Compounds in sortable tables) - https://app.knovel.com/web/view/itable/show.v/rcid:kpKS000009/cid:kt00395F16/viewerType:itble/

II.  IR

A.  Spectra Collections (IR)
      1. IR - Liquid or Solution
            NIMC site - http://sdbs.db.aist.go.jp/sdbs/cgi-bin/cre_index.cgi 
              NIST site - http://webbook.nist.gov/chemistry/ 
            PSLC -  http://pslc.uwsp.edu/
            Aldrich, Sigma - https://www.sigmaaldrich.com/united-states.html
            Gasmet - https://www.gasmet.com/de/produkte/tools/spectrum-library/
  
      2. IR - Gas Phase
            NIST -  http://webbook.nist.gov/chemistry/ 
            Gasmet - https://www.gasmet.com/de/produkte/tools/spectrum-library/

B.  Group Frequencies

   3.  Analysis Approach

IR Analysis - https://www.masterorganicchemistry.com/2016/11/23/quick_analysis_of_ir_spectra/

III.  NMR

A.  Spectra Collections  (nmr)   
     1.  HNMR - Experimental 
            NIMC site - http://sdbs.db.aist.go.jp/sdbs/cgi-bin/cre_index.cgi?lang=eng
            PSLC -  http://pslc.uwsp.edu/
            Aldrich, Sigma - https://www.sigmaaldrich.com/united-states.html 
                        
            Solvents - http://www2.chem.umd.edu/nmr/reference/isotope_solvent.pdf
            Deuterated solvents - http://www.wiredchemist.com/chemistry/data/common_nmr_solvents.html 
             Bioorganics - http://mmcd.nmrfam.wisc.edu/mmcdbrowse.html
          

     2.  HNMR - Calculated
            ChemExper Chem Directory -  http://www.chemexper.com/ 
            nmrdb - http://www.nmrdb.org/ 
           
    3.   13CNMR - Experimental
            NIMC site - http://sdbs.db.aist.go.jp/sdbs/cgi-bin/cre_index.cgi?lang=eng
            PSLC -  http://pslc.uwsp.edu/

B.  Chemical Shifts 

IV.  MASS SPECTROMETRY

A.  Spectra Collections  (ms)
      NIMC site - http://sdbs.db.aist.go.jp/sdbs/cgi-bin/cre_index.cgi?lang=eng
      PSLC -  http://pslc.uwsp.edu/
                       
      Pherobase - http://www.pherobase.com/database/compound/compounds-index.php 
      human metabolites - http://www.hmdb.ca/

 

 

 

B.  Fragments Lost

Ion  Fragment Lost  Possible Inference 

P-1

H 

P-15

CH3

P-16

NH2

amide

P-17 OH
P-18 H2O alcohol
P-19 F  fluoro compound
P-26 C2H2  aromatic
P-28 CO 
N2 
C2H4  		 ketone 

aromatic, ethyl ether, ethyl ester, n-propyl ketones, McLafferty 
rearrangement

P-29 CHO 
C2H5 		 aldehyde 
ethyl

P-30

CH2=NH2

primary amine

P-31

OCH3 

methyl ester

P-32

CH3OH   

methyl ester

P-35, 37

Cl

chloro compound

P-43 C3H7 
CH3CO		 propyl 
methyl ketone
P-45 CO2H    carboxylic acid
P-46 NO2  nitro aromatic
P-57 C4H9 butyl
P-60 CH3CO2H  acetate
P-79,81 Br  bromo cmpd.

C.  Fragments

Fragment   Possible Group Possible Inference 
29  CHO+, C2H5+
30 CH2=NH2+ primary amine
31 CH2=OH+ primary alcohol
41 C3H5+ allyl group
43 C3H7+  
CH3CO+  		 propyl group 
acyl group
50 C4H2+  aromatic
51 C4H3+ phenyl group
57 C4H9+  
C2H5CO+		 butyl group 
ethyl ketone, propionate ester 
58 CH2=C(OH)CH3+  methyl ketone (McL. Rear.)
59 CO2CH3+ 
CH2=C(OH)NH2+		 methyl ester   .
primary amide (McL. Rear.) 
60 CH2=C(OH)OH+  carboxylic acid (McL. Rear.) 
71 C5H11+ 
C3H7CO+		 pentyl group 
propyl ketone, butyrate ester  
74 CH2=C(OH)OCH3+ methyl ester (McL. Rear.)
76 C6H4+  mono or disubstituted benzene
77 C6H5+ phenyl
85, 99 CcH2c+1+  benzyl group
91 C7H7+  alkyl group
105 C6H5CO+  benzoyl group

V.  UV-Vis

A.  Spectra Collections (uv-vis)
    NIST - site - http://webbook.nist.gov/chemistry/
    OMLC - http://omlc.org/spectra/PhotochemCAD/html/alpha.html

B.  Analysis - https://www.masterorganicchemistry.com/2016/09/16/introduction-to-uv-vis-spectroscopy/

VI.  REACTIONS, SYNTHESIS

A.  Compilations of Reactions
    http://www.name-reaction.com/ 
    http://www.orgsyn.org/
    http://www.monomerchem.com/display4.html 
      http://www.chemthes.com/rxn-type.php
    http://cssp.chemspider.com/ 
    http://www.organic-chemistry.org/reactions.htm
    https://organicchemistrydata.org/links/#reaction_info
    http://chemistrybydesign.oia.arizona.edu/
    http://www.synarchive.com/

B.  Reaction-Map of Organic Chemistry
    http://murov.info/Reaction-Map.htm     http://murov.info/rxnmaponline.pdf
        Exercises based on Rxn-map - http://murov.info/orgchemrxnexe.htm     http://murov.info/orgchemrxnexe.pptx

 

VII.  LABORATORY EXPERIMENTS

 

A.  Techniques
      https://open.umn.edu/opentextbooks/textbooks/36
      https://www.cpp.edu/~lsstarkey/ochemlab/
      http://www.ochem.com/ 
      http://www.oc-praktikum.de/nop/ 
       http://library.sciencemadness.org/library/books/Research_Techniques_in_Organic_Chemistry.pdf 
      http://do.chem.uni.wroc.pl/system/files/Organic chemistry - laboratory methods_201617_0.pdf

B.  Distillations

1.  Distillation Plates

 

2.  Boiling Points Under Reduced Pressure

For general use, the nomograph below enables estimation of boiling points at reduced pressure from boiling points at atmospheric pressure.  Many laboratory vacuum distillations are conducted using an aspirator to reduce the pressure. Combining the Clausius-Clapeyron equation with an empirically adjusted Trouton's rule results in the approximate equation for the boiling point at reduced pressure (18 mm):

Tw  =  0.78 Ta - 60    where Tw  =  the bp at water aspirator pressure (assumed to be 18 mm) in Celsius
                                                        and Ta  =  bp at atmospheric press. (760 mm) in Celsius.

 

C.  Safety

        http://web.centre.edu/labsafety/handbook.htm    
       https://www.cdc.gov/niosh/docs/2007-107/pdfs/2007-107.pdf
       https://www.nyu.edu/content/dam/nyu/environmentalHealthSafety/documents/LabSafetyManual.pdf
       https://fens.sabanciuniv.edu/sites/fens.sabanciuniv.edu/files/lab-safety/labsafety_web.pdf
       https://www.ehs.washington.edu/resource/laboratory-safety-manual-510
       https://www.osha.gov/Publications/laboratory/OSHA3404laboratory-safety-guidance.pdf

 

 D.  Experiments
       http://murov.info/orglab.htm
       http://faculty.chas.uni.edu/~manfredi/860-121/ORG LAB MAN S08.pdf
       https://www.bths.edu/ourpages/auto/2014/1/5/47316574/orgo-labs.pdf
       http://www.unesco.org/science/doc/Organi_chem_220709_FINAL.pdf
       http://www.ch.ic.ac.uk/GIC/organic_lab.html

 

VIII.  HISTORY of ORGANIC CHEMISTRY

 

A.  Timeline
      http://murov.info/organicmilestones.htm


B.  History
      https://en.wikipedia.org/wiki/Organic_chemistry
      https://www.encyclopedia.com/science/science-magazines/chemistry-organic-chemistry

 

IX.  PERIODIC TABLES

 

A.  Samples
      http://www.webelements.com/
      http://murov.info/periodictables.htm  
      http://murov.info/aufbaupt.htm

 

B.  Collections
      https://www.meta-synthesis.com/webbook/35_pt/pt_database.php?Button=All
      https://digital.sciencehistory.org/collections/6w924c45h

 

C.  Element Properties
      http://www.rsc.org/periodic-table/ 
      http://www.chemicool.com/
      http://www.knowledgedoor.com/

 

D.  Periodic Trends
      https://periodictable.com/Properties/A/CrustAbundance.html
      http://chemwiki.ucdavis.edu/Core/Inorganic_Chemistry/Descriptive_Chemistry/Periodic_Trends_of_Elemental_Properties/Periodic_Trends
      http://environmentalchemistry.com/yogi/periodic/
      http://murov.info/pertabtrends.htm
     

E.  Directories
      http://murov.info/periodictables.htm
      http://www.martindalecenter.com/Reference_3_PerTables.html 
       http://www.martindalecenter.com/Reference_3_PerTables.html 
      http://www.thecatalyst.org/m03ptabl.html 

 

F.  Timeline
        http://murov.info/timelines.htm

 

X. ELECTRONEGATIVITY VALUES

     http://www.meta-synthesis.com/webbook/36_eneg/electroneg.html 
     https://periodictable.me/electronegativity-chart/
     http://www.knowledgedoor.com/

 

XI.  HAMMETT PARAMETERS

      http://www.wiredchemist.com/chemistry/data/hammett_sigma_constants.html
     http://old.iupac.org/publications/pac/1997/pdf/6912x2497.pdf

 

XII.  pH INDICATORS, pKa VALUES

A.  pH Indicators

https://www.compoundchem.com/2014/04/04/the-colours-chemistry-of-ph-indicators/
https://en.wikipedia.org/wiki/PH_indicator        
ttps://www.sciencecompany.com/ph_indicator_ranges.aspx     
https://www.techknow.org.uk/wiki/index.php?title=PH
http://foundoutaboutchemistry.blogspot.com/2016/05/acid-base-indicator-charts.html

B.  pKa Values
         https://www2.chem.wisc.edu/areas/reich/pkatable/index.htm
         http://www.wiredchemist.com/chemistry/data/acid_constants.html
         http://www.wiredchemist.com/chemistry/data/base_constants.html
         http://www.zirchrom.com/organic.htm
         http://ccc.chem.pitt.edu/wipf/MechOMs/evans_pKa_table.pdf

 

XIII.  ORGANIC CHEMISTRY DIRECTORIES 

         https://organicchemistrydata.org/
        http://www.organicworldwide.net/   

 

XIV.  MOLECULAR MODELS (drawing programs)


https://www.acdlabs.com/resources/freeware/chemsketch/index.php

https://chemaxon.com/products/marvin-js

 

XV.  EDUCATION

 

A.  Online Textbooks

https://www.masterorganicchemistry.com/
https://www2.chemistry.msu.edu/faculty/reusch/VirtTxtJml/intro1.htm    
https://www2.chemistry.msu.edu/faculty/reusch/VirtTxtJml/intro1a.htm
https://chem.libretexts.org/Bookshelves/Organic_Chemistry/Book%3A_Virtual_Textbook_of_OChem_(Reusch)_UNDER_CONSTRUCTION
http://www.ochem.com 
https://www.chemguide.co.uk/orgpropsmenu.html
http://chemthes.com/rxn-type.php
https://en.wikibooks.org/wiki/Organic_Chemistry
http://en.wikibooks.org/wiki/Organic_Chemistry     
http://www.stolaf.edu/depts/chemistry/courses/toolkits/247/  

organic laboratory manual - http://murov.info/orglab.htm

         http://www.stolaf.edu/depts/chemistry/courses/toolkits/247/ 

B.  Chemical Education Journals

       J. Chem. Ed. -  http://pubs.acs.org/journal/jceda8
                                       http://pubs.acs.org/loi/jceda8 
         Education                           Education in Chemistry - http://www.rsc.org/eic/
                                              http://www.rsc.org/eic/e-magazine
        Chem13 News - https://uwaterloo.ca/chem13-news-magazine/

 

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