Amines

=Amines = Austin Davy, Liz Doherty, Joe Wioncek   **__media type="file" key="Amines LJA.m4a" width="330" height="330"

SCRIPT__** Austin: Our group has focused on a specific type of organic compounds called amines. Joe: Amines are chemical compounds which are closely related to ammonia, or NH3. Austin: An alkyl group is: "a functional group of an organic compound containing carbon and hydrogen atoms." Joe: Based upon the number of alkyl groups attached to the molecule, amines are divided into three main groups: primary, secondary, and tertiary. Liz: There are also "quaternary" amines, but they are not as common, since they involve the attachment of four alkyl groups. Austin: The structure of a primary amine has only one alkyl group attached to the molecule. ***Show picture of methylamine/primary amine (Picture 3)*** Joe: Secondary amines have a structure consisting of two alkyl groups attached to the molecule. Liz: Finally tertiary amines have three alkyl groups bonded to the molecule. Joe: For the most part, the nomenclature of amines follows systematic patterns based on whether the amine is primary, secondary, or tertiary. Liz: More complex amines, however, have names which call for memorization as opposed to following a pattern, like alkyl+amine for a primary amine. **<span style="font-size: 90%; font-family: Georgia,serif;">*Show picture of naming systems (Picture 10)* ** Austin: When naming an amine there are three systems of nomenclature; IUPAC, Chemical Abstract, and common. Joe: The IUPAC system approaches naming an amine by naming amine functions as substitutents on the largest alkyl group in the compound. This system is very detailled and complex. Liz: Our research does not cover the IUPAC system in depth but, in general, the IUPAC system follows three basic rules... Austin: **1.** A root or base indicating a major chain or ring of carbon atoms Joe: Our podcast focuses on the two other major naming systems: the Chemical Abstract (or CA) and the common system of nomenclature. Liz: Listen carefully to the next segment which covers the CA and common systems of naming amines. Austin: To determine the name of the amine you must first acknowledge how many alkyl groups are attached to the nitrogen atom. Joe: This will give you the basis of if it is a primary, secondary, or tertiary amine. Liz: After determining what **type** of amine, there is a system of nomenclature that applies to each. <span style="font-size: 70%; font-family: Georgia,serif;"><span style="font-size: 90%; font-family: Georgia,serif;">**<span style="font-size: 170%; font-family: Georgia,serif;">*Show examples of naming picture (Picture 6)* ** Austin: Starting with the primary group you name these amines by writing the alkyl group first followed by the word amine. An example of this is Methyl amine. Joe: Another way of naming amines in the primary group is by writing their names as one. To accomplish this the alkyl is changed to an alkan then the word amine is attached to the end. Methanamine is an example of this naming method. <span style="display: block; font-size: 130%; font-family: Georgia,serif; text-align: left;">**<span style="font-family: Georgia,serif;">*Show methylamine (Picture 3) leave on through secondary amine naming section* ** Liz: If the amine being named is a secondary amine, the root name of the secondary amine will be the alkyl amine or alkanamine with the //longest carbon chain,// followed by the __next__ chain which is attached to the nitrogen atom. Austin: In addition, the N representing the nitrogen atom is placed ahead because it is a lower locant than numbered locants. An example of a named secondary amine is N-methylmethyl amine or N-methylmethanamine, dimethyl amine. Joe: In naming a tertiary amine the root name is given to the alkyl amine or alkanamine with the longest chain just as it was in the secondary amines. The other chains in the chemical are located off of the nitrogen atom as substituents. Liz: Unlike the primary and secondary amines, a tertiary amine begins with N,N followed by the amine because this is a result of their being two substituents off of the nitrogen atom. Austin: Some examples of tertiary amines include N,N-dimethylmethyl amine, N,N-dimethylemthamine, trimethylamine,morphine, and quinine. <span style="display: block; font-size: 130%; font-family: Georgia,serif; text-align: left;">Joe: Now that the naming system of amines has been addressed, it's important to recognize the practical importance of amines. Austin: Amines are raw materials in drugs and vitamins, such as benzedrines. Liz: They are also used as raw materials to manufacture synthetics. For example, an amine called aniline is essential in the production of synthetic dyes. Joe: Other uses of amines include: antioxidants for rubber and roofing asphalt, stabilizers for cellulose nitrate explosives, anticling/waterproofing agents for textiles, and fabric softeners. <span style="font-size: 110%; font-family: Georgia,serif;">***Show examples of liquid detergents (Picture 8)*** Austin: They are also found in liquid detergents, personal care products, car waxes, and furniture polishes. Liz: Beyond these practical uses, amines are found in nature. In fact, they are the "constituents of amino acids," which are the building blocks of proteins. Also, the bases of nucleic acids DNA and RNA are amines. Joe: We also know that amines are closely related to the ammonia molecule found in nature. Austin: A definite characteristic of an amine is that the nitrogen atom has a lone pair of electrons. Liz: So, it can accept an H+ ion to bond with it to form a positive ammonium ion. Joe: Because of the lone pair of electrons, amines are more highly soluble. Austin: Amines are well known for having a foul odor. Liz: The foul odor is most commonly caused by the amines cadaverina and putresine. Joe: Beyond the standard types of amines (primary, secondary, and tertiary), we thought we should mention a few examples of heterocyclic amines before concluding. Austin: Some examples include pyridine, piperidine, and imidazole. <span style="font-size: 110%; font-family: Georgia,serif;">***Show picture of these amines (Picture 7)*** Liz: We strived to provide you with the most well-rounded and extensive information on amines as possible. Joe: We hope our in-depth research of amines was beneficial to your knowledge. <span style="display: block; font-size: 130%; font-family: Georgia,serif; text-align: left;">
 * Show picture of ammonia molecule (Picture 1)*** <span style="display: block; font-size: 130%; font-family: Georgia,serif; text-align: left;">Liz: They form when the hydrogen atoms in an ammonia molecule are replaced by hydrocarbon or alkyl groups.
 * Show picture of alkyl group (Picture 2)***
 * <span style="font-size: 110%; font-family: Georgia,serif;">*Show picture of diethylamine/secondary amine (Picture 4)* **
 * <span style="font-size: 90%; font-family: Georgia,serif;">*Show picture of trimethylamine/tertiary amine (Picture 5)* **  <span style="display: block; font-size: 130%; font-family: Georgia,serif; text-align: left;">Austin: By looking at the structure of a chemical, it can be classified as an amine if it consists of a nitrogen atom bonded to either hydrogen atom, or alkyl groups which are imperative structural features.
 * 2.** A suffix which designates functional groups
 * 3.** Names of substituent/alkyl groups, other than hydrogen
 * <span style="font-size: 110%; font-family: Georgia,serif;">*Picture of Morphine (Picture 11)* **
 * <span style="font-size: 110%; font-family: Georgia,serif;">*Picture of benzedrine inhaler (Picture 13)* **
 * <span style="font-size: 110%; font-family: Georgia,serif;">*Show picture of fabric softener (Picture 9)* **
 * <span style="font-size: 110%; font-family: Georgia,serif;">*Show DNA/RNA base picture (Picture 12)* **

<span style="font-family: Impact,Charcoal,sans-serif;"> __What are Amines?__ <span style="font-family: Georgia,serif;">Amines are chemical compounds which are closely related to ammonia, which is written as NH3. Amines form when the hydrogen atoms in an ammonia molecule are replaced by hydrocarbon groups. Amines are divided into three main groups; primary, secondary, and tertiary. There are also "quaternary" amines, but they are not typically included as "standard" amines. For example, R4N is known as a quaternary amine salt, since //four// (not one, two, or three) alkyl groups are attached to the nitrogen atom and also four hydrogen atoms are being replaced by these groups.

<span style="font-size: 120%; font-family: Georgia,serif;"><span style="font-size: 130%; font-family: Georgia,serif;"><span style="font-size: 120%; font-family: Georgia,serif;"><span style="font-family: Georgia,serif;"><span style="font-size: 70%; font-family: Georgia,serif;">⌘**__EXAMPLES OF AMINES__**: Amines are classified according to the number of alkyl groups attached to the nitrogen atom present, as well as the number of hydrogen atoms replaced by these hydrocarbon groups.

Examples: methylamine, trimethylamine, dimethylamine
 * A)** Primary amines= 1 hydrogen atom in ammonia molecule is replaced.

Examples: dimethylamine, diethylamine
 * B)** Secondary amines= 2 hydrogen atoms in ammonia molecule are replaced.

Examples: trimethylamine, morphine, quinine
 * C)** Tertiary amines= All hydrogen atoms in ammonia molecule are replaced.

Examples: pyridine, pyrrole, indole, quinoline <span style="font-size: 130%; font-family: Georgia,serif;"> __**Some characteristics of Amines...**__ -Amines more soluble because of hydrogen bonding between water molecules and lone electrons -Nitrogen atom in amines has a lone pair of electrons, so it can accept an H+ ion to bond to the nitrogen, forming a positive ammonium ion -Foul odor due mostly to amines called cadaverine and putresine <span style="font-size: 120%; font-family: Georgia,serif;"><span style="font-size: 130%; font-family: Georgia,serif;"><span style="font-size: 120%; font-family: Georgia,serif;"><span style="font-family: Georgia,serif;"><span style="font-size: 70%; font-family: Georgia,serif;">     <span style="font-size: 130%; font-family: Georgia,serif;"><span style="font-size: 130%; font-family: Georgia,serif;"> <span style="font-family: Georgia,serif;"><span style="font-family: Georgia,serif;"><span style="font-size: 130%; font-family: Georgia,serif;">⌘__**STRUCTURE**__: 1. Primary Amine- ONE alkyl group bonded to the nitrogen atom. 2. Secondary Amine- TWO alkyl groups bonded to the nitrogen atom. 3. Tertiary Amine- THREE alkyl groups bonded to the nitrogen atom.
 * D)** Heterocyclic amines= Amines whose nitrogen atoms exist as parts of rings

<span style="font-size: 130%; font-family: Georgia,serif;">⌘**__INFO ON HOW CHEMICALS CAN BE RECOGNIZED (FROM STRUCTURES)__**: <span style="font-size: 130%; font-family: Georgia,serif;">-Amines contain an important structural feature: a nitrogen atom joined by 3 bonds to either //<span style="font-size: 130%; font-family: Georgia,serif;">hydrogen atom or alkyl groups // //-//<span style="font-size: 130%; font-family: Georgia,serif;">__Alkyl group*__=A "Functional" group of an organic chemical containing carbon/hydrogen atoms //*[Definition provided by]:// [|//http://www.greenfacts.org/glossary/abc/alkyl-group-alkylation-alkylate.htm//]

<span style="font-size: 130%; font-family: Georgia,serif;">⌘**__NAMING AMINES__**: <span style="font-family: Georgia,serif;">**Intro:** For the most part, the names of amines follow systematic patterns based on whether they are primary or secondary/tertiary. More complex amines, however, have names which call for memorization as opposed to following a pattern, like alkyl+amine for a primary amine. For example, NH2 is named aniline because it is a heterocyclic amine which means its nitrogen is part of a ring. <span style="background-color: rgb(255, 255, 255);"> <span style="color: rgb(215, 96, 15);"><span style="color: rgb(0, 0, 0); background-color: rgb(254, 220, 220);"><span style="background-color: rgb(255, 255, 255);"><span style="font-size: 130%; font-family: Georgia,serif;">In order to name an amine:
 * FIRST** Determine the amount of alkyl groups that are attached to the nitrogen atom (or the presence of other special groups).

//<span style="color: rgb(0, 0, 0); background-color: rgb(254, 220, 220);"><span style="background-color: rgb(255, 255, 255);"><span style="font-size: 130%; font-family: Georgia,serif;">**Primary Amines**- the alkyl is written first followed by the word amine. Ex: Methyl amine Another way to name an Amine as one word is changing the alkyl to an alkan then attaching amine. Ex: Methanamine

// <span style="color: rgb(215, 96, 15);"><span style="color: rgb(0, 0, 0); background-color: rgb(254, 220, 220);"><span style="background-color: rgb(255, 255, 255);"><span style="font-size: 130%; font-family: Georgia,serif;">Ex: N//-methylmethyl amine// N   <span style="color: rgb(0, 0, 0);"><span style="color: rgb(215, 96, 15);"><span style="color: rgb(0, 0, 0); background-color: rgb(254, 220, 220);"><span style="background-color: rgb(255, 255, 255);"><span style="font-size: 130%; font-family: Georgia,serif;">-methylmethanamine dimethyl amine
 * Secondary Amines-** The root name of a secondary amine is the alkyl amine or alkanamine with the longest carbon chain followed by the next chain or substituent which is attached to the N. The N is placed ahead because it is a lower locant than numbered locants.

//**Tertiary Amines**- To name a tertiary amine the root name is given to the alkyl amine or alkanamine with the longest carbon chain. The other chanis are located off of the N as substituents. The name starts with N,N then the amine because this is a result of their being two substituents off of the N atom.// Ex: N,N-dimethylmethyl amine N,N-dimethylemthamine trimethyl amine    <span style="color: rgb(0, 0, 0);"><span style="color: rgb(215, 96, 15);"><span style="background-color: rgb(255, 255, 255);"><span style="background-color: rgb(255, 255, 255);"><span style="color: rgb(0, 0, 0); background-color: rgb(254, 220, 220);"><span style="font-size: 130%; font-family: Georgia,serif;"> <span style="font-size: 130%; font-family: Georgia,serif;"> ⌘**__WHERE CAN AMINES BE FOUND IN NATURE?__**: -"Constituents of amino acids," which are the building blocks of proteins -Bases of nucleic acids DNA and RNA are amines -Ammonia (NH3) <span style="font-family: Georgia,serif;"> ⌘**__USE OF AMINES__**: <span style="font-size: 70%; font-family: Georgia,serif;"><span style="font-family: Georgia,serif;"><span style="font-family: Georgia,serif;"><span style="font-size: 130%; font-family: Georgia,serif;"><span style="font-family: Georgia,serif;"><span style="font-size: 130%; font-family: Georgia,serif;">-Used in drugs/vitamins (ex: benzedrine) Raw materials to manufacture synthetics (ex: aniline, an amine, is essential in the production of synthetic dyes)     <span style="display: block; font-size: 130%; font-family: Georgia,serif; text-align: left;"><span style="font-size: 70%; font-family: Georgia,serif;"><span style="font-family: Georgia,serif;"><span style="font-family: Georgia,serif;"><span style="font-size: 130%; font-family: Georgia,serif;">-Antioxidants for rubber and roofing asphalt (ex: diarylamines)     <span style="display: block; font-size: 130%; font-family: Georgia,serif; text-align: left;"><span style="font-size: 70%; font-family: Georgia,serif;"><span style="font-family: Georgia,serif;"><span style="font-family: Georgia,serif;"><span style="font-size: 130%; font-family: Georgia,serif;">-Stabilizers for cellulose nitrate explosives (ex: diphenylamines)     <span style="display: block; font-size: 130%; font-family: Georgia,serif; text-align: left;"><span style="font-size: 70%; font-family: Georgia,serif;"><span style="font-family: Georgia,serif;"><span style="font-family: Georgia,serif;"><span style="font-size: 130%; font-family: Georgia,serif;">-Anticling/waterproofing agents for textiles     <span style="display: block; font-size: 130%; font-family: Georgia,serif; text-align: left;"><span style="font-size: 70%; font-family: Georgia,serif;"><span style="font-family: Georgia,serif;"><span style="font-family: Georgia,serif;"><span style="font-size: 130%; font-family: Georgia,serif;">-Fabric softeners     <span style="display: block; font-size: 130%; font-family: Georgia,serif; text-align: left;"><span style="font-size: 70%; font-family: Georgia,serif;"><span style="font-family: Georgia,serif;"><span style="font-family: Georgia,serif;"><span style="font-size: 130%; font-family: Georgia,serif;">-In paper coating -Found in liquid detergents, personal care products, car waxes, and furniture polishes <span style="font-size: 70%; font-family: Georgia,serif;"><span style="font-size: 120%; font-family: Georgia,serif;"> <span style="font-size: 130%; font-family: Georgia,serif;"> <span style="font-size: 130%; font-family: Georgia,serif;">»__SOURCES__: <span style="font-family: Georgia,serif;"><span style="font-family: Georgia,serif;">1) <span style="font-family: Georgia,serif;">http://www.chemguide.co.uk/organicprops/amines/background.html <span style="font-family: Georgia,serif;"><span style="font-family: Georgia,serif;">2)  <span style="font-family: Georgia,serif;">http://hyperphysics.phy-astr.gsu.edu/Hbase/Organic/amine.html <span style="font-family: Georgia,serif;"><span style="font-family: Georgia,serif;">3) <span style="font-family: Georgia,serif;">http://chemistry2.csudh.edu/rpendarvis/aminbassyn.html <span style="font-family: Georgia,serif;"><span style="font-family: Georgia,serif;">4)  <span style="font-family: Georgia,serif;">http://www.greenfacts.org/glossary/abc/alkyl-group-alkylation-alkylate.htm <span style="font-family: Georgia,serif;"><span style="font-family: Georgia,serif;">5) <span style="font-family: Georgia,serif;">http://www.chem.ucalgary.ca/courses/350/Carey/nomenclature/amines/amines-1.html <span style="font-family: Georgia,serif;"><span style="font-family: Georgia,serif;">6)  <span style="font-family: Georgia,serif;">http://intro.chem.okstate.edu/1014/Lecture/FunctionalGroup/FuncGrp3.html <span style="font-family: Georgia,serif;"><span style="font-family: Georgia,serif;">7) <span style="font-family: Georgia,serif;">[|http://www.cem.msu.edu/~reusch/VirtualText/amine1.htm] <span style="font-family: Georgia,serif;"><span style="font-family: Georgia,serif;">8)  <span style="font-family: Georgia,serif;">http://www.ilpi.com/msds/ref/amine.html <span style="font-family: Georgia,serif;"><span style="font-family: Georgia,serif;">9) __<span style="color: rgb(0, 0, 255);">[|www.uncw.edu/chem/Courses/Martinn/chm212martin/Amines.ppt] __ 10) http://www.huntsman.com/performance_products/ShowPage.cfm?PageID=862 11) http://hyperphysics.phy-astr.gsu.edu/Hbase/Organic/amine.html 12) [|http://www.cem.msu.edu/~reusch/VirtualText/amine1.htm] 13) [|http://www.cem.msu.edu/~reusch/VirtualText/nomen1.htm#start]

<span style="font-size: 130%; font-family: Georgia,serif;"> »__PICTURES__: <span style="font-family: Georgia,serif;">1) <span style="font-family: Georgia,serif;">http://uh.edu/engines/epi2287.htm <span style="font-family: Georgia,serif;">2) <span style="font-family: Georgia,serif;">http://www.hcc.mnscu.edu/chem/V.18/alkyl_group_defn.jpg <span style="font-family: Georgia,serif;">3) <span style="font-family: Georgia,serif;">http://upload.wikimedia.org/wikipedia/commons/7/7f/Methylamine-2D.png 4) <span style="font-family: Georgia,serif;">http://upload.wikimedia.org/wikipedia/commons/thumb/1/1b/Diethylamine_structure.svg/220px-Diethylamine_structure.svg.png <span style="font-family: Georgia,serif;">5) <span style="font-family: Georgia,serif;">http://commons.wikimedia.org/wiki/File:Trimethylamine_structure.svg <span style="font-family: Georgia,serif;">6) http://www.cliffsnotes.com/WileyCDA/CliffsReviewTopic/Introduction-to-Amines.topicArticleId-23297,articleId-23288.html <span style="font-family: Georgia,serif;"> <span style="font-family: Georgia,serif;">7) [|http://www.auburn.edu/~rileytn/py420/graphics/hetbases.gif] <span style="font-family: Georgia,serif;"> 8) http://ecx.images-amazon.com/images/I/51in5dFOZcL._SL500_AA280_.jpg 9) http://www.oppictures.com/singleimages/400/RAC74035CT_1_2.JPG 10) [|http://www.cem.msu.edu/~reusch/VirtualText/amine1.htm] 11) http://z.about.com/d/chemistry/1/0/f/e/morphine.jpg 12) http://www.mcat45.com/images/Nucleotide-bases-mcat.png 13) http://wings.buffalo.edu/aru/benzedrine.jpg